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

HRID 1644321
Notes
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Reaction equation

HRID 1644321 reaction equation
[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.C(OC(=O)NC1CCN(CCN2C3C(=CC=C(F)C=3F)C=CC2=O)CC1)(C)(C)C.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]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 5

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

Product 1

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

Procedure

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%).

Sources & evidence

ORD record
ord-8a4f247b2a5e49db9d4b7d4321aefc51
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08124602B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes