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 1481229ノート

反応式

HRID 1481229 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-6f0f02f28d1d4b9aa97333ebb94001e3
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

反応ノート

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