Methanol → 3-(S)-[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-3-pyridin-3-yl-propionic acid methyl ester

HRID 1481224노트

반응식

HRID 1481224 반응식
CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].Cl.Cl.[CH2:27]([O:29][C:30](=[O:40])[CH2:31][C@H:32]([NH2:39])[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)C.C[O-].[Na+].CO>>[CH3:27][O:29][C:30](=[O:40])[CH2:31][C@H:32]([NH:39][C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH:9]=2)=[O:4])[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1

참가 물질

5

반응물 4

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 44891224Ethyl (3S)-3-amino-3-(pyridin-3-yl)propanoate--hydrogen chloride (1/2)HCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

생성물 1

HCID 898131423-(S)-[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-3-pyridin-3-yl-propionic acid methyl ester수율 56.1%

반응 조건

온도
140 °C

실험 절차

1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.156 mmol) was combined in a CEM microwave tube (10 mL) with (S)-3-amino-3-pyridin-3-yl-propionic acid ethyl ester dihydrochloride (134 mg, 0.5 mmol) (commercially available from AstaTech 46247) and a solution of sodium methoxide in methanol (2 mL, 0.5M, 1 mmol) was added with stirring. The reaction was heated to 140° C. in the CEM microwave apparatus for approximately 90 minutes. The reaction was cooled, concentrated under vacuum and filtered through silica to provide 41 mg of the desired product which was used without additional purification.

후처리

  1. additionwas added
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated under vacuum
  4. filtrationfiltered through silica

출처 및 근거

ORD 기록
ord-0eb44f8c39fe448f9fe13c846152b084
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

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