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1-[2-氟-6-(三氟甲基)苄基]-6-甲基嘧啶-2,4(1H,3H)-二酮 | 830346-47-9

物质功能分类

医药中间体 - 原料药中间体

分子结构分类

有机化合物 - 苯类化合物 - 苯和取代衍生物

中文名称

1-[2-氟-6-(三氟甲基)苄基]-6-甲基嘧啶-2,4(1H,3H)-二酮

中文别名

噁拉戈利中间体4；1-(2-氟-6-三氟甲基-苄基)-6-甲基-1H-嘧啶-2,4-二酮；1-(2-氟-6-(三氟甲基)苄基)-6-甲基嘧啶-2,4(1H,3H)-二酮

英文名称

1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione

英文别名

1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methylpyrimidine-2,4-dione

1-[2-氟-6-(三氟甲基)苄基]-6-甲基嘧啶-2,4(1H,3H)-二酮化学式

CAS

830346-47-9

化学式

C₁₃H₁₀F₄N₂O₂

mdl

——

分子量

302.228

InChiKey

IJRKKZXPXBTHER-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

密度：

1.413±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

2.1
重原子数：

21
可旋转键数：

2
环数：

2.0
sp3杂化的碳原子比例：

0.23
拓扑面积：

49.4
氢给体数：

1
氢受体数：

6

安全信息

海关编码：

2933599090
危险性防范说明：

P261,P305+P351+P338
危险性描述：

H302,H315,H319,H335
储存条件：

室温下应存放在干燥密封的容器中。

SDS

SDS：c022476b8952a6ca2fb71184442481fa

查看

制备方法与用途

用途

恶拉戈利中间体4可用作医药中间体。

上下游信息

下游产品

中文名称	英文名称	CAS号	化学式	分子量
5-溴-1-(2-氟-6-(三氟甲基)苄基)-4-羟基-6-甲基嘧啶-2(1H)-酮	5-bromo-1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione	830346-48-0	C₁₃H₉BrF₄N₂O₂	381.124
1-[2-氟-6-(三氟甲基)苄基]-5-碘-6-甲基嘧啶-2,4(1h,3h)-二酮	1-[2-fluoro-6-(trifluoromethyl)benzyl]-5-iodo-6-methyl-3H-pyrimidine-2,4-dione	1150560-54-5	C₁₃H₉F₄IN₂O₂	428.125
——	5-bromo-1-[2-fluoro-6-trifluoromethyl-benzyl]-6-methyl-3-[2(R)-amino-2-phenylethyl]-pyrimidine-2,4-(1H,3H)-dione	2617827-21-9	C₂₁H₁₈BrF₄N₃O₂	500.29
5-(2-氟-3-甲氧基苯基)-1-[[2-氟-6-(三氟甲基)苯基]甲基]-6-甲基-2,4(1H,3H)-嘧啶二酮	5-(2-fluoro-3-methoxyphenyl)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione	1150560-59-0	C₂₀H₁₅F₅N₂O₃	426.343
N-[(1R)-2-[5-溴-3-[[2-氟-6-(三氟甲基)苯基]甲基]-3,6-二氢-4-甲基-2,6-二氧代-1(2H)-嘧啶基]-1-苯基乙基]氨基甲酸叔丁酯	tert-butyl (R)-(2-(5-bromo-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-1-phenylethyl)carbamate	830346-49-1	C₂₆H₂₆BrF₄N₃O₄	600.408
——	P693YA5SU6	869984-34-9	C₂₇H₂₈BrF₄N₃O₅	630.434
——	tert-butyl N-[(1S)-3-[5-bromo-3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-4-methyl-2,6-dioxopyrimidin-1-yl]-1-(2-methoxyphenyl)propyl]carbamate	869984-30-5	C₂₈H₃₀BrF₄N₃O₅	644.461
——	tert-butyl N-[2-[5-bromo-3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-4-methyl-2,6-dioxopyrimidin-1-yl]-1-(2-hydroxyphenyl)ethyl]carbamate	869984-51-0	C₂₆H₂₆BrF₄N₃O₅	616.407
——	3-(2-{(S)-1-amino-3-[3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-5-phenyl-3,6-dihydro-2H-pyrimidin-1-yl]-propyl}-phenoxy)-propionic acid	——	C₃₁H₂₉F₄N₃O₅	599.582
——	(2-{(S)-1-amino-3-[3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-5-phenyl-3,6-dihydro-2H-pyrimidin-1-yl]-propyl}-phenoxy)-acetic acid	——	C₃₀H₂₇F₄N₃O₅	585.555
——	tert-butyl N-[2-[5-bromo-3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-4-methyl-2,6-dioxopyrimidin-1-yl]-1-(2-methoxyphenyl)ethyl]carbamate	869984-25-8	C₂₇H₂₈BrF₄N₃O₅	630.434
——	ethyl 4-[2-[(1S)-3-[5-bromo-3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-4-methyl-2,6-dioxopyrimidin-1-yl]-1-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]phenoxy]butanoate	869984-35-0	C₃₃H₃₈BrF₄N₃O₇	744.578
——	4-(2-{(S)-1-amino-3-[3-(2-fluoro-6-trifluoromethyl-benzyl)-5-(3-isopropyl-phenyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-propyl}-phenoxy)-butyric acid	——	C₃₅H₃₇F₄N₃O₅	655.689
——	tert-butyl N-[(1S)-3-[3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-4-methyl-2,6-dioxo-5-phenylpyrimidin-1-yl]-1-(2-hydroxyphenyl)propyl]carbamate	869984-32-7	C₃₃H₃₃F₄N₃O₅	627.636
——	tert-butyl N-[2-[5-bromo-3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-4-methyl-2,6-dioxopyrimidin-1-yl]-1-[2-(cyanomethoxy)phenyl]ethyl]carbamate	869984-48-5	C₂₈H₂₇BrF₄N₄O₅	655.444
——	(R)-3-(2-amino-2-phenylethyl)-5-(2-fluoro-3-methoxyphenyl)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione	830346-50-4	C₂₈H₂₄F₅N₃O₃	545.509
——	tert-butyl N-[(1S)-3-[3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-4-methyl-2,6-dioxo-5-phenylpyrimidin-1-yl]-1-(2-methoxyphenyl)propyl]carbamate	869984-31-6	C₃₄H₃₅F₄N₃O₅	641.663
——	ethyl 4-[2-[(1S)-3-[3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-4-methyl-2,6-dioxo-5-(3-propan-2-ylphenyl)pyrimidin-1-yl]-1-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]phenoxy]butanoate	869984-36-1	C₄₂H₄₉F₄N₃O₇	783.861
(R)-4-((2-(5-(2-氟-3-甲氧苯基)-3-(2-氟-6-(三氟甲基)苯甲基)-4-甲基-2,6-二氧代-2,3-二氢嘧啶-1(6H)–基)-1-苯乙基)氨基)正丁酸乙酯	ethyl (R)-4-((2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-1-phenylethyl)amino)butanoate	832720-84-0	C₃₄H₃₄F₅N₃O₅	659.653
——	5-(2-{1-amino-2-[5-(2-fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-ethyl}-phenoxy)-pentanoic acid	——	C₃₃H₃₂F₅N₃O₆	661.626
N-[(1R)-2-[5-(2-氟-3-甲氧基苯基)-3-[[2-氟-6-(三氟甲基)苯基]甲基]-3,6-二氢-4-甲基-2,6-二氧代-1(2H)-嘧啶基]-1-苯基乙基]氨基甲酸叔丁酯	tert-butyl (R)-(2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-1-phenylethyl)carbamate	830346-51-5	C₃₃H₃₂F₅N₃O₅	645.626

反应信息

作为反应物：

描述：

1-[2-氟-6-(三氟甲基)苄基]-6-甲基嘧啶-2,4(1H,3H)-二酮在溴、溶剂黄146 作用下，生成 5-溴-1-(2-氟-6-(三氟甲基)苄基)-4-羟基-6-甲基嘧啶-2(1H)-酮

参考文献：

名称：

Elagolix 钠盐及其合成中间体：光谱学、晶体学和构象研究

摘要：

Elagolix 钠盐是第一个上市的口服活性非肽类促性腺激素释放激素受体拮抗剂 (GnRHR-ant)，用于治疗激素依赖性疾病，例如子宫内膜异位症和子宫肌瘤。尽管该药物自 2018 年上市以来，仍缺乏对该药物及其合成中间体的全面核磁共振分析。因此，为了填补这一文献空白，我们在这里进行了详细的核磁共振研究，从而实现了 1H、13C 和 15N NMR 信号的完整分配。在构象分析的支持下，这些数据允许确定两种阻转异构体的立体化学特征，可在溶液中检测到。此外，这些后者也通过基于纤维素的手性 HPLC 检测到，从通过针对报告的已实施合成程序制备的样品开始。总的来说，这些结果有助于进一步理解药物发现中的阻转异构现象，并可用于设计安全稳定的类似物，从而提高目标选择性。

DOI：

10.3390/molecules28093861
作为产物：

描述：

2-氟-6-(三氟甲基)苯甲醛在盐酸、盐酸羟胺、氢气、碳酸氢钠、 sodium hydroxide 作用下，以四氢呋喃、甲醇、乙醇、水、 N,N-二甲基甲酰胺、异丙醇为溶剂， 15.0~130.0 ℃ 、300.01 kPa 条件下，反应 14.0h，生成 1-[2-氟-6-(三氟甲基)苄基]-6-甲基嘧啶-2,4(1H,3H)-二酮

参考文献：

名称：

[EN] PROCESSES TO PRODUCE ELAGOLIX
[FR] PROCESSUS DE PRODUCTION D'ÉLAGOLIX

摘要：

本发明涉及一种用于制备依诺司特及其盐和中间化合物的可扩展工艺。

公开号：

WO2019112968A1

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文献信息

[EN] PROCESSES FOR THE PREPARATION OF URACIL DERIVATIVES [FR] PROCÉDÉS DE PRÉPARATION DE DÉRIVÉS D'URACILE

申请人：NEUROCRINE BIOSCIENCES INC

公开号：WO2009062087A1

公开（公告）日：2009-05-14

The present invention relates to processes and intermediates for preparing Gonadotropin-Releasing Hormone (GnRH) receptor antagonists of structure (VI); and stereoisomers and pharmaceutically acceptable salts thereof.

本发明涉及制备促性腺激素释放激素（GnRH）受体拮抗剂结构（VI）的过程和中间体，以及其立体异构体和药用盐。
[EN] URACIL-TYPE GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS AND METHODS RELATED THERETO [FR] ANTAGONISTES DE TYPE URACIL GONADOLIBÉRINE ET LES MÉTHODES AFFÉRENTES

申请人：NEUROCRINE BIOSCIENCES INC

公开号：WO2005113516A1

公开（公告）日：2005-12-01

Compounds having utility as GnRH receptor antagonists and for treatment of a variety of sex-hormone related conditions in both men and women. Such compounds have the following structure (I): (I) wherein R1a, R1b, R1c, R2a, R2b, R3, R4, R5, R6, R7, n and X are as defined herein, including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof. Also disclosed are compositions containing a compound of structure (I) in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for antagonizing gonadotropin-releasing hormone in a subject in need thereof.

具有作为GnRH受体拮抗剂的效用，并用于治疗男性和女性的各种与性激素相关疾病的化合物。这些化合物具有以下结构（I）：（I）其中R1a、R1b、R1c、R2a、R2b、R3、R4、R5、R6、R7、n和X如本文所定义，包括立体异构体、前药和其药用可接受盐。还公开了含有结构（I）化合物的组合物，与药用可接受载体结合，以及与使用该组合物拮抗需要该物质的受试者中的促性腺激素释放激素相关的方法。
[EN] PYRIMIDINE-2, 4-DIONE DERIVATIVES AS GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS [FR] DERIVES DE PYRIMIDINE-2, 4-DIONE UTILISES COMME ANTAGONISTES DU RECEPTEUR D'HORMONE LIBERANT DE LA GONADOTROPHINE

申请人：NEUROCRINE BIOSCIENCES INC

公开号：WO2005007165A1

公开（公告）日：2005-01-27

GnRH receptor antagonists are disclosed that have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have the structure: wherein R1a, R1b, R1c, R2a, R2b, R3, R4, R5, R6 and X are as defined herein, including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof. Also disclosed are compositions containing a compound of this invention in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for antagonizing gonadotropin-releasing hormone in a subject in need thereof.

GnRH受体拮抗剂被披露，对男性和女性的各种与性激素相关的疾病具有治疗作用。本发明的化合物具有以下结构：其中R1a、R1b、R1c、R2a、R2b、R3、R4、R5、R6和X的定义如本文所述，包括立体异构体、前药和其药用可接受盐。还披露了含有本发明化合物的组合物与药用可接受载体的组合物，以及与在需要时对抗性腺激素释放激素的使用方法。
[EN] PYRIMIDINE-2,4-DIONE DERIVATIVES AS GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS [FR] DERIVES DE PYRIMIDINE-2,4-DIONE, SERVANT D'ANTAGONISTES AU RECEPTEUR DE L'HORMONE DE LIBERATION DE LA GONADOTROPINE

申请人：NEUROCRINE BIOSCIENCES INC

公开号：WO2005007164A1

公开（公告）日：2005-01-27

GnRH receptor antagonists are disclosed that have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have the structure formula (I) wherein R1a, R1b, R2a, R2b, R3, R4, R5, R6, R7 and X are as defined herein, including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof. Also disclosed are compositions containing a compound of this invention in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for antagonizing gonadotropin-releasing hormone in a subject in need thereof.

GnRH受体拮抗剂已被披露，可用于治疗男性和女性的各种与性激素相关的疾病。本发明的化合物具有结构式（I），其中R1a、R1b、R2a、R2b、R3、R4、R5、R6、R7和X如本文所定义，包括立体异构体、前药和其药用盐。此外，还披露了含有本发明化合物的组合物，该组合物与药用载体结合，以及涉及使用该组合物来拮抗需要此类治疗的受试者的促性腺激素释放激素的方法。
[EN] GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS AND METHODS RELATING THERETO [FR] ANTAGONISTES DES RECEPTEURS DES HORMONES LIBERANT DES GONADOTROPINES ET PROCEDES CONNEXES

申请人：NEUROCRINE BIOSCIENCES INC

公开号：WO2005007633A1

公开（公告）日：2005-01-27

GnRH receptor antagonists are disclosed that have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have the structure: wherein n, R1a, R1b, R1c, R2a, R2b, R3, R4, R5, R6 and X are as defined herein, including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof. Also disclosed are compositions containing a compound of this invention in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for antagonizing gonadotropin-releasing hormone in a subject in need thereof.

抑制性激素释放激素受体拮抗剂已经被披露，可用于治疗男性和女性的多种与性激素相关的疾病。本发明的化合物具有以下结构：其中n、R1a、R1b、R1c、R2a、R2b、R3、R4、R5、R6和X如本文所定义，包括立体异构体、前药和其药用可接受的盐。还披露了含有本发明化合物的组合物，以及与药用可接受载体结合的方法，用于拮抗需要的受试者体内的促性腺激素释放激素。