N-methoxy-N-methyl-5,6-dihydro-4H-pyrrolo-[1,2-b]pyrazole-2-carboxamide | 799781-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡唑类
• 英文名称: N-methoxy-N-methyl-5,6-dihydro-4H-pyrrolo-[1,2-b]pyrazole-2-carboxamide
• 英文别名: N-methoxy-N-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxamide
• CAS: 799781-97-8
• 化学式: C₉H₁₃N₃O₂
• 分子量: 195.221
• InChiKey: FWHHOSCDELSADD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methoxy-N-methyl-5,6-dihydro-4H-pyrrolo-[1,2-b]pyrazole-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以67%的产率得到5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carbaldehyde
  参考文献：
  名称：

  Process for synthesizing beta-lactamase inhibitor intermediates

  摘要：

  提供了一种制备具有结构式I的双环杂环芳基羰基的方法，其中X和Y在规范中定义。这些双环杂环芳基羰基在β-内酰胺酶抑制剂的制备中作为中间体是有用的。

  公开号：

  US20040242874A1
• 作为产物：
  描述：

  potassium 5,6-dihydro-4H-pyrrolo-[1,2-b]pyrazole-2-carboxylate 在 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 N-methoxy-N-methyl-5,6-dihydro-4H-pyrrolo-[1,2-b]pyrazole-2-carboxamide
  参考文献：
  名称：

  Selective Hydrolysis of Ethyl 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate and Ethyl 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate as a Key Step in the Large-Scale Synthesis of Bicyclic Heteroaryl Carboxyaldehydes

  摘要：

  The isomeric mixture of ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2- and -3-carboxylates ( 14 and 15), derived from a proline meso-ionic synthon, demonstrated remarkably different stabilities towards alkaline hydrolysis. On that basis, a non-chromatographic, highly efficient method for their large-scale separation was developed. The desired isomer 14 was converted into 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carbaldehyde, a key intermediate in the synthesis of bicyclic heteroaryl-substituted 6-alkylidene penems.

  DOI：

  10.1021/op050218b

文献信息

• Production of bicyclic-heteroaryl-2-carboxylic acids by selective enzymatic hydrolysis of a mixture of positional esters
  申请人：Wyeth Holdings Corporation

  公开号：US20040229324A1

  公开（公告）日：2004-11-18

  The invention relates to an enzymatic process for the production of an intermediate, bicyclic-heteroaryl-2-carboxylic acid, of the formula 1 wherein X and Y are defined in the specification and which are useful in the preparation of beta-lactamase inhibitors, by selective enzymatic hydrolysis of a mixture of positional hydrolyzable esters of the formulae 2 where X, Y, and R are defined in the specification.

  本发明涉及一种酶法生产中间体双环杂芳基-2-羧酸的方法，其化学式为1，其中X和Y在规范中定义，并且在β-内酰胺酶抑制剂的制备中有用，通过选择性酶解式2的可位水解酯混合物来实现，其中X、Y和R在规范中定义。
• PROCESS FOR SYNTHESIZING ß-LACTAMASE INHIBITOR INTERMEDIATES
  申请人：Wyeth Holdings Corporation

  公开号：EP1626972A1

  公开（公告）日：2006-02-22
• US7276611B2
  申请人：——

  公开号：US7276611B2

  公开（公告）日：2007-10-02
• US7316917B2
  申请人：——

  公开号：US7316917B2

  公开（公告）日：2008-01-08
• [EN] PROCESS FOR SYNTHESIZING beta-LACTAMASE INHIBITOR INTERMEDIATES<br/>[FR] PROCESSUS DE SYNTHESE D'INTERMEDIAIRES DE L'INHIBITEUR DE 20041202WO03093277A1WYETH CORP [US], et al20031113Claims 1-16; p. 5, l. 32-p. 7, l. 3; example 21PX1-63PXEP1241170A2PFIZER LTD [GB], et al20020918p. 29, route A, step iv); preparations 28-29X1-63,1-19,60A20-59,61-63XAJ.N. LEE ET AL.: "Synthesis of New Pyrazolylisoxazolines via 1,3-Dipolar Cycloaddition Reaction of Bicyclic Sydnone with Benzyl Propiolate", BULL. KORENA CHEM. SOC., vol. 21, no. 8, 2000, pages 761 - 762, XP002300479J.N. LEE ET AL.Synthesis of New Pyrazolylisoxazolines via 1,3-Dipolar Cycloaddition Reaction of Bicyclic Sydnone with Benzyl PropiolateBULL. KORENA CHEM. SOC.2000218761762Scheme 1, steps 1) to 4)X1-63,1-19,60A20-59,61-63XAWO9410178A1SMITHKLINE BEECHAM PLC [GB], et al19940511Claim 13; preparations 1-5; p. 8, l. 17-p. 13, l. 2A1-63AEP0084892A2SUMITOMO CHEMICAL CO [JP]19830803Claim 1p. 2, l. 8-p. 5, last lineA1-63ASCHMID A ET AL: "INDUSTRIAL BIOCATALYSIS TODAY AND TOMORROW", NATURE, MACMILLAN JOURNALS LTD. LONDON, GB, vol. 409, 11 January 2001 (2001-01-11), pages 258 - 268, XP000985347, ISSN: 0028-0836SCHMID A ET ALINDUSTRIAL BIOCATALYSIS TODAY AND TOMORROWNATURE, MACMILLAN JOURNALS LTD. LONDON, GB200101114090028-0836258268Fig. 2 and 4A1-63AB.G. DAVIS; V. BOYER: "Biocatalysis and enzymes in organic synthesis", NAT. PROD. REP., vol. 18, 2001, pages 618 - 640, XP002300480B.G. DAVIS; V. BOYERBiocatalysis and enzymes in organic synthesisNAT. PROD. REP.200118618640Point 2.1, Table 1; Point 2.2, schemes 9-10 and 15, Table 3A1-63A
  申请人：WYETH CORP

  公开号：WO2004104008A1

  公开（公告）日：2004-12-02

  The invention relates to an enzymatic process for the production of an intermediate, bicyclic-heteroaryl-2-carboxylic acid, of the formula (I) wherein X and Y are defined in the specification and which are useful in the preparation of beta-lactamase inhibitors, by selective enzymatic hydrolysis of a mixture of positional hydrolyzable esters of the formula (II) and (III) where X, Y and R are defined in the specification.