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

HRID 255200ノート

反応式

HRID 255200 の反応式
[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]

参加物

6

反応物 5

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 642082495,7-Difluoro-1,2-dihydroquinolin-2-one2 回HCID 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 methanesulfonate2 回

生成物 1

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

実験手順

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%).

出典と根拠

ORDレコード
ord-4be2bbcb67ff4e3193b48c3b4ba07c68
出典データセット
uspto-grants-2011_01
特許番号
US07875715B2

反応ノート

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