1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-{[7-Cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carbonyl]amino}-2-cyclopropyl-propionic acid tert-butyl ester

HRID 1481229노트

반응식

HRID 1481229 반응식
[C:1]([O:5][C:6](=[O:13])[CH:7]([CH:10]1[CH2:12][CH2:11]1)[CH2:8][NH2:9])([CH3:4])([CH3:3])[CH3:2].C(O[C:17]([C:19]1[N:20]=[C:21](C#N)[C:22]2[C:27]([C:28]=1[OH:29])=[CH:26][CH:25]=[C:24]([O:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)[CH:23]=2)=[O:18])C.C1CCN2[C:42](=[N:43]CCC2)CC1>CC(N(C)C)=O>[C:1]([O:5][C:6](=[O:13])[CH:7]([CH:10]1[CH2:12][CH2:11]1)[CH2:8][NH:9][C:17]([C:19]1[N:20]=[CH:21][C:22]2[C:27]([C:28]=1[OH:29])=[CH:26][CH2:25][C:24]([C:42]#[N:43])([O:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)[CH:23]=2)=[O:18])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 89812868Tert-butyl 3-amino-2-cyclopropylpropanoateHCID 898130801-Cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester

생성물 1

HCID 1178437943-{[7-Cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carbonyl]amino}-2-cyclopropyl-propionic acid tert-butyl ester

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
150 °C

실험 절차

A mixture of 3-amino-2-cyclopropyl-propionic acid tert-butyl ester (39 mg), 1-cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester (28 mg) and DBU (0.019 mL) in DMA (0.5 mL) was heated in an oil bath (150° C.) for 1 h. The reaction mixture was then partitioned between EtOAc and diluted HCl solution, EtOAc phase was separated and washed with water, diluted NaCl solution and dried over anhydrous sodium sulfate solution, filtered, concentrated and silica gel column purified to give desired product (21 mg). LC-MS ESI+: 475 (M+1)+.

후처리

  1. customThe reaction mixture was then partitioned between EtOAc and diluted HCl solution, EtOAc phase
  2. customwas separated
  3. washwashed with water, diluted NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate solution
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customsilica gel column purified

출처 및 근거

ORD 기록
ord-6f0f02f28d1d4b9aa97333ebb94001e3
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

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