Methylamine → Regadenoson

HRID 39122

반응식

HRID 39122 반응식
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:20]1[CH:24]=[C:23]([C:25]([O:27]CC)=O)[CH:22]=[N:21]1)=[N:14][C:15]=2[NH2:19].[CH3:30][NH2:31]>>[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:20]1[CH:24]=[C:23]([C:25]([NH:31][CH3:30])=[O:27])[CH:22]=[N:21]1)=[N:14][C:15]=2[NH2:19]

참가 물질

3

반응물 2

HCID 6329MethylamineHCID 9865974Ethyl 1-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-yl)-1H-pyrazole-4-carboxylate

생성물 1

HCID 219024Regadenoson

실험 절차

A mixture of ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxylate (46.4 g) and methylamine (40% in water, 600 ml) was stirred at ambient temperature for about 4 hours, following the progress of the reaction by HPLC analysis. The majority of the excess methylamine was removed under reduced pressure, and the remaining mixture cooled at 0° C. for 2 hours. The solid material was filtered off, washed with ice-cold 200 proof ethanol, and dried under reduced pressure, to provide (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazol-4-yl)-N-methylcarboxamide as its monohydrate, 36.6 g, purity 99.6%.

후처리

  1. customthe progress of the reaction by HPLC analysis
  2. customThe majority of the excess methylamine was removed under reduced pressure
  3. temperaturethe remaining mixture cooled at 0° C. for 2 hours
  4. filtrationThe solid material was filtered off
  5. washwashed with ice-cold 200 proof ethanol
  6. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-4fc3ebe9260b447da8652e6be6d9c972
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524883B2

연결된 노트

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