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N-(2,6-dichloro-3-pyridinyl)-5-bromo-2-ethylamino-3-pyridinecarboxamide | 189393-13-3

分子结构分类

有机化合物 - 有机杂环化合物 - 吡啶及其衍生物

中文名称

——

中文别名

——

英文名称

N-(2,6-dichloro-3-pyridinyl)-5-bromo-2-ethylamino-3-pyridinecarboxamide

英文别名

5-bromo-N-(2,6-dichloropyridin-3-yl)-2-(ethylamino)pyridine-3-carboxamide

N-(2,6-dichloro-3-pyridinyl)-5-bromo-2-ethylamino-3-pyridinecarboxamide化学式

CAS

189393-13-3

化学式

C₁₃H₁₁BrCl₂N₄O

mdl

——

分子量

390.067

InChiKey

XACLTUVKPGGQEV-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

193-194 °C
沸点：

450.1±45.0 °C(Predicted)
密度：

1.690±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

4.5
重原子数：

21
可旋转键数：

4
环数：

2.0
sp3杂化的碳原子比例：

0.15
拓扑面积：

66.9
氢给体数：

2
氢受体数：

4

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	N-(2,6-dichloro-3-pyridinyl)-2-ethylamino-3-pyridinecarboxamide	189393-12-2	C₁₃H₁₂Cl₂N₄O	311.17
——	N-(2,6-dichloro-3-pyridinyl)-2-chloro-3-pyridinecarboxamide	189393-11-1	C₁₁H₆Cl₃N₃O	302.547

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	8-bromo-2-chloro-5,11-dihydro-11-ethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189393-15-5	C₁₃H₁₀BrClN₄O	353.606
8-溴-2-氯-11-乙基-5-甲基-5,11-二氢-6H-二吡啶并[3,2-B:2',3'-E][1,4]二氮杂卓-6-酮	8-Bromo-2-chloro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]-diazepin-6-one	189393-17-7	C₁₄H₁₂BrClN₄O	367.632
——	2-amino-8-bromo-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189394-89-6	C₁₄H₁₄BrN₅O	348.202
——	8-bromo-2-fluoro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]-diazepin-6-one	189393-18-8	C₁₄H₁₂BrFN₄O	351.178
——	2-chloro-5,11-dihydro-11-ethyl-8-chloromethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	949568-68-7	C₁₄H₁₂Cl₂N₄O	323.181
——	2-chloro-5,11-dihydro-11-ethyl-8-hydroxymethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	949568-67-6	C₁₄H₁₃ClN₄O₂	304.736
——	13-Bromo-2-ethyl-5-[(4-methoxyphenyl)methylamino]-9-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one	211436-36-1	C₂₂H₂₂BrN₅O₂	468.353
——	2-chloro-5,11-dihydro-11-ethyl-8-(phenylthio)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₀H₁₇ClN₄OS	396.9
——	2-chloro-5,11-dihydro-11-ethyl-8-formyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189391-87-5	C₁₅H₁₃ClN₄O₂	316.747
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(phenylamino)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₂₀ClN₅O	393.876
——	5-Chloro-2-ethyl-9-methyl-13-{[methyl(phenyl)amino]methyl}-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one	——	C₂₂H₂₂ClN₅O	407.903
——	8-(3-aminophenylamino)methyl-2-chloro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₂₁ClN₆O	408.89
——	8-(N-Methyl-N-phenyl)carboxamido-2-chloro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₂H₂₀ClN₅O₂	421.886
——	2-chloro-5,11-dihydro-11-ethyl-8-(3-methoxyphenylthio)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₁₉ClN₄O₂S	426.926
——	2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189391-90-0	C₁₅H₁₄Cl₂N₄O	337.208
——	2-chloro-5,11-dihydro-11-ethyl-8-hydroxymethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189391-89-7	C₁₅H₁₅ClN₄O₂	318.763
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-vinyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189393-43-9	C₁₆H₁₅ClN₄O	314.774
——	2-chloro-5,11-dihydro-11-ethyl-8-hydroxy-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189392-00-5	C₁₄H₁₃ClN₄O₂	304.736
——	5-Chloro-2-ethyl-9-methyl-10-oxo-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene-13-carboxylic acid	211436-40-7	C₁₅H₁₃ClN₄O₃	332.746
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(pyrid-4-yloxy)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₀H₁₈ClN₅O₂	395.848
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(phenyloxy)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₁₉ClN₄O₂	394.86
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(N-oxo-pyrid-4-yloxy)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189392-04-9	C₂₀H₁₈ClN₅O₃	411.848
——	8-(3-aminophenyloxy)methyl-2-chloro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₂₀ClN₅O₂	409.875
——	2-chloro-5,11-dihydro-11-ethyl-8-(4-hydroxyphenyloxy)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₁₉ClN₄O₃	410.86
——	5-Chloro-2-ethyl-13-(3-hydroxyphenoxymethyl)-9-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one	——	C₂₁H₁₉ClN₄O₃	410.86
——	2-chloro-5,11-dihydro-11-ethyl-8-(4-fluorophenyloxy)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₁₈ClFN₄O₂	412.851
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(3-pyridyloxy)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₀H₁₈ClN₅O₂	395.848
——	8-(3-(N,N-Dimethylamino)phenyloxy)methyl-2-chloro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₃H₂₄ClN₅O₂	437.929
——	2-chloro-5,11-dihydro-11-ethyl-8-(2-methylpyrid-4-yloxy)methyl-5-methyl-6H-dipyrido[3,2-b;2',3'-e][1,4]diazepin-6-one	——	C₂₁H₂₀ClN₅O₂	409.875
——	4-({5-Chloro-2-ethyl-9-methyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-13-yl}methoxy)-2-methyl-1-oxidopyridin-1-ium	——	C₂₁H₂₀ClN₅O₃	425.875
——	2-chloro-5,11-dihydro-11-ethyl-8-(2-hydroxyphenyloxy)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₁₉ClN₄O₃	410.86
——	2-chloro-5,11-dihydro-11-ethyl-8-(4-(methoxycarbonyl)phenyloxy)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₃H₂₁ClN₄O₄	452.897
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(pyrid-4-ylthio)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₀H₁₈ClN₅OS	411.915
——	2-chloro-5,11-dihydro-11-ethyl-8-{(phenyl)thiomethyl}-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189392-52-7	C₂₁H₁₉ClN₄OS	410.927
——	7-Chloro-5-ethyl-2-(3-fluoro-phenoxymethyl)-10-methyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one	——	C₂₁H₁₈ClFN₄O₂	412.851
——	2-chloro-5,11-dihydro-11-ethyl-8-(2-fluorophenyloxy)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₁₈ClFN₄O₂	412.851
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-phenylmethoxy-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₁₉ClN₄O₂	394.86
——	5,11-dihydro-11-ethyl-2-fluoro-8-formyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189391-92-2	C₁₅H₁₃FN₄O₂	300.292
——	2-chloro-5,11-dihydro-11-ethyl-8-(3-(carboxy)phenyloxy)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189392-42-5	C₂₂H₁₉ClN₄O₄	438.87
——	5-Chloro-2-ethyl-9-methyl-13-(3-nitrophenoxymethyl)-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one	189392-14-1	C₂₁H₁₈ClN₅O₄	439.858
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(2-trifluoromethylpyrid-4-yloxy)methyl-6H-dipyrido[3,2-b;2',3'-e][1,4]diazepin-6-one	——	C₂₁H₁₇ClF₃N₅O₂	463.846
——	Methyl 3-({5-chloro-2-ethyl-9-methyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-13-yl}methoxy)benzoate	189392-40-3	C₂₃H₂₁ClN₄O₄	452.897
——	5,11-dihydro-11-ethyl-2-fluoro-8-hydroxymethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189391-93-3	C₁₅H₁₅FN₄O₂	302.308
——	8-(3-(aminocarbonyl)phenyloxy)methyl-2-chloro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₂H₂₀ClN₅O₃	437.885
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(N-oxo-2-trifluoromethylpyrid-4-yloxy)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	189392-10-7	C₂₁H₁₇ClF₃N₅O₃	479.846
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(phenylsulfonyl)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₁₉ClN₄O₃S	442.926
——	2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(phenylsulfinyl)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₁H₁₉ClN₄O₂S	426.926
——	2-chloro-5,11-dihydro-11-ethyl-8-(2-(methoxycarbonyl)phenyloxy)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	——	C₂₃H₂₁ClN₄O₄	452.897

反应信息

作为反应物：

描述：

N-(2,6-dichloro-3-pyridinyl)-5-bromo-2-ethylamino-3-pyridinecarboxamide 在吡啶、 sodium tetrahydroborate 、四(三苯基膦)钯、氯化亚砜、 2,3-二巯基丁二酸、水、 sodium hexamethyldisilazane 、 sodium hydride 、臭氧、三乙胺作用下，以四氢呋喃、氯仿、 N,N-二甲基甲酰胺为溶剂，反应 5.67h，生成 2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

参考文献：

名称：

HIV-1逆转录酶的新型非核苷抑制剂。8. 8-芳氧基甲基-和8-芳硫基甲基二吡啶二ze庚酮。

摘要：

奈韦拉平（I）是第一种获得监管机构批准的人类免疫缺陷病毒1型（HIV-1）非核苷逆转录酶（RT）抑制剂。作为围绕奈韦拉平三环核心系统的第二代计划的结果，2-氯-5，11-二氢-11-乙基-5-甲基-8-（2-（吡啶-4-基）乙基）-6H -dipyrido [3，2-b：2'，3'-e] [1,4]二氮杂-6-6（II）1a和2-氯-5，11-二氢-11-乙基-5-甲基-已鉴定出8-苯基乙基-6H-二吡啶并[3,2-b：2'，3'-e] [1,4]二氮杂pin-6-一（III）1a是广谱HIV-1 RT抑制剂。给出了替换II或III的8-乙基连接基的亚甲基的详细检查。已发现8-芳氧基甲基和8-芳硫基甲基是对RT的效力的优选取代方式。进一步针对一组具有临床意义的突变RT酶（K103N，V106A，G190A，P236L）以及在细胞毒性和体外代谢分析中对最有效的化合物进行了评估。最有效的化合物

DOI：

10.1021/jm9707030
作为产物：

描述：

2,6-二氯-3-氨基吡啶在吡啶、溴、 potassium acetate 作用下，以 1,4-二氧六环、环己烷、溶剂黄146 、 xylene 为溶剂，反应 16.75h，生成 N-(2,6-dichloro-3-pyridinyl)-5-bromo-2-ethylamino-3-pyridinecarboxamide

参考文献：

名称：

Novel 2-Chloro-8-arylthiomethyldipyridodiazepinone Derivatives with Activity against HIV-1 Reverse Transcriptase

摘要：

根据对Y181CHIV-1 RT的分子模型分析，合成了含有未取代的内酰胺氮和2-氯-8-芳基硫甲基的二吡啶二氮杂烷衍生物，采用了一种高效的合成路线。其中一些化合物的抗病毒活性被评估，针对HIV-1 RT亚型E，发现它们表现出与一些临床使用的治疗药物相当的抗病毒活性。

DOI：

10.3390/12020218

点击查看最新优质反应信息

文献信息

8-arylalkyl- and

申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

公开号：US05705499A1

公开（公告）日：1998-01-06

Disclosed are novel 8-arylalkyl-5,11-dihydro-6H-dipyrido\x9b3,2-b:2',3'-e!\x9b1,4!diazepines. These are useful in the treatment of HIV-1 infection.

公开的是新型的8-芳基烷基-5,11-二氢-6H-二吡啶[3,2-b:2',3'-e]![1,4]二氮杂环。这些化合物在治疗HIV-1感染中是有用的。
Dipyridodiazepinone derivatives; synthesis and anti HIV-1 activity

作者：Nisachon Khunnawutmanotham、Nitirat Chimnoi、Arunee Thitithanyanont、Patchreenart Saparpakorn、Kiattawee Choowongkomon、Pornpan Pungpo、Supa Hannongbua、Supanna Techasakul

DOI：10.3762/bjoc.5.36

日期：——

Ten dipyridodiazepinone derivatives were synthesized and evaluated for their anti HIV-1 reverse transcriptase activity against wild-type and mutant type enzymes, K103N and Y181C. Two of them were found to be promising inhibitors for HIV-1 RT.

合成了十种二吡啶基二氮杂环己酮衍生物，并针对野生型和突变型酶K103N和Y181C评估它们对HIV-1逆转录酶的抑制活性。其中有两种被发现是有希望的HIV-1 RT抑制剂。
8-Arylalkyl- and 8-arylheteroalkyl-5, 11-dihydro-6H-dipyrido-[3,2-b:2', 3'-e][1,4]diazepines and their use in the prevention or treatment of HIV infection

申请人：BOEHRINGER INGELHEIM PHARMACEUTICALS INC.

公开号：EP0767172B1

公开（公告）日：2003-03-26
US5705499A

申请人：——

公开号：US5705499A

公开（公告）日：1998-01-06
Novel Nonnucleoside Inhibitors of HIV-1 Reverse Transcriptase. 8. 8-Aryloxymethyl- and 8-Arylthiomethyldipyridodiazepinones

作者：Charles L. Cywin、Janice M. Klunder、MaryAnn Hoermann、Janice R. Brickwood、Eva David、Peter M. Grob、Racheline Schwartz、Daniel Pauletti、Kevin J. Barringer、Cheng-Kon Shih、Christopher L. Sorge、David A. Erickson、David P. Joseph、Susan E. Hattox

DOI：10.1021/jm9707030

日期：1998.7.1

Nevirapine (I) is the first human immunodeficiency virus type 1 (HIV-1) nonnucleoside reverse transcriptase (RT) inhibitor to reach regulatory approval. As a result of a second generation program around the tricyclic core system of nevirapine, 2-chloro-5, 11-dihydro-11-ethyl-5-methyl-8-(2-(pyridin-4-yl)ethyl)-6H-dipyrido[3, 2-b:2',3'-e][1,4]diazepin-6-one (II)1a and 2-chloro-5, 11-dihydro-11-ethyl

奈韦拉平（I）是第一种获得监管机构批准的人类免疫缺陷病毒1型（HIV-1）非核苷逆转录酶（RT）抑制剂。作为围绕奈韦拉平三环核心系统的第二代计划的结果，2-氯-5，11-二氢-11-乙基-5-甲基-8-（2-（吡啶-4-基）乙基）-6H -dipyrido [3，2-b：2'，3'-e] [1,4]二氮杂-6-6（II）1a和2-氯-5，11-二氢-11-乙基-5-甲基-已鉴定出8-苯基乙基-6H-二吡啶并[3,2-b：2'，3'-e] [1,4]二氮杂pin-6-一（III）1a是广谱HIV-1 RT抑制剂。给出了替换II或III的8-乙基连接基的亚甲基的详细检查。已发现8-芳氧基甲基和8-芳硫基甲基是对RT的效力的优选取代方式。进一步针对一组具有临床意义的突变RT酶（K103N，V106A，G190A，P236L）以及在细胞毒性和体外代谢分析中对最有效的化合物进行了评估。最有效的化合物