2-Fluoroadenosine → Regadenoson

HRID 60618

반응식

HRID 60618 반응식
F[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[CH3:21][NH:22][C:23]([C:25]1[CH:26]=[N:27][NH:28][CH:29]=1)=[O:24]>C(#N)C.CS(C)=O>[CH3:21][NH:22][C:23]([C:25]1[CH:26]=[N:27][N:28]([C:2]2[N:3]=[C:4]([NH2:20])[C:5]3[N:6]=[CH:7][N:8]([C:18]=3[N:19]=2)[C@@H:9]2[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[CH:29]=1)=[O:24]

참가 물질

4

반응물 2

HCID 89752-FluoroadenosineHCID 43582329N-Methyl-1H-pyrazole-4-carboxamide

생성물 1

HCID 219024Regadenoson

시약·촉매·용매 1

HCID 22251437Acetonitrile dimethylsulfoxide용매

실험 절차

PCT application WO 2012/149196 describes preparation of polymorph D by a relatively complicated procedure. First, a “cross coupling” reaction of 2-fluoroadenosine with N-methylpyrazol-4-carboxamide in an acetonitrile/dimethylsulfoxide mixture provides crude 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine, which is then purified by reverse-phase chromatography using a methanol/water mixture. After concentrating at 150° C. under reduced pressure, polymorph D is obtained as a white solid substance containing variable amounts of water.

후처리

  1. custompreparation of polymorph D by a relatively complicated procedure

출처 및 근거

ORD 기록
ord-d5b8c544639640a1a3d8d0b2a2d1e656
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441006B2

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