Potassium Carbonate → Cis(+/-)1-{2-[4-azido-3-hydroxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one

HRID 255200노트

반응식

HRID 255200 반응식
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[NH:7]2.[H-].[Na+].CS(O[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][C@H:26]([N:29]=[N+:30]=[N-:31])[C@H:25]([OH:32])[CH2:24]1)(=O)=O.FC1C(F)=C2C(C=CC(=O)N2CCN2CCC(NC(=O)OC(C)(C)C)CC2)=CC=1.C(=O)([O-])[O-].[K+].[K+]>>[N:29]([C@H:26]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][N:7]2[C:8]3[C:3](=[C:2]([F:1])[CH:11]=[C:10]([F:12])[CH:9]=3)[CH:4]=[CH:5][C:6]2=[O:13])[CH2:24][C@H:25]1[OH:32])=[N+:30]=[N-:31]

참가 물질

6

반응물 5

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 642082495,7-Difluoro-1,2-dihydroquinolin-2-one2회HCID 86642603tert-butyl{1-[2-(7,8-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamateHCID 86642609Cis(+/-)2-(4-azido-3-hydroxypiperidin-1-yl)ethyl methanesulfonate2회

생성물 1

HCID 86642608Cis(+/-)1-{2-[4-azido-3-hydroxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one

실험 절차

5,7-Difluoroquinolin-2(1H)-one (Intermediate 25) (389 mg, 2.15 mmol) was deprotonated with sodium hydride (95 mg, 60% in oil, 2.36 mmol) and alkylated with cis(±) 2-(4-azido-3-hydroxypiperidin-1-yl)ethyl methanesulfonate (Intermediate 44) (2.15 mmol) as described for Intermediate 20, except after 24 hours, potassium carbonate (100 mg, 0.72 mmol) was added and the resulting mixture was stirred for another 24 hours at room temperature to give the product as a colorless hard foam, 195 mg (26%).

출처 및 근거

ORD 기록
ord-4be2bbcb67ff4e3193b48c3b4ba07c68
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875715B2

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