Water → HCID 71522919, compound

HRID 2178541Notes

Reaction equation

HRID 2178541 reaction equation
[F:1][C:2]([F:10])(S(F)(=O)=O)C(O)=O.[OH:11][C:12]1[N:17]=[C:16]([CH:18]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]3[C:26]([N:31]4[CH2:36][CH2:35][CH2:34][CH2:33][C:32]4=[O:37])=[N:27][CH:28]=[CH:29][CH:30]=3)[CH2:19]2)[CH:15]=[CH:14][CH:13]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].O>C(#N)C>[F:1][CH:2]([F:10])[O:11][C:12]1[N:17]=[C:16]([CH:18]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]3[C:26]([N:31]4[CH2:36][CH2:35][CH2:34][CH2:33][C:32]4=[O:37])=[N:27][CH:28]=[CH:29][CH:30]=3)[CH2:19]2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 178516074HCID 178516074, compound

Product 1

HCID 71522919HCID 71522919, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,2-Difluoro-2-(fluorosulfonyl)acetic acid (9.72 mg, 0.054 mmol, 1 eq) is added slowly, under stirring, to a mixture of 1-(3-{2-[3-(6-hydroxypyridin-2-yl)pyrrolidin-1-yl]ethyl}pyridin-2-yl)piperidin-2-one a16-1 (20 mg, 0.054 mmol, 1 eq) and dry sodium sulfate (0.78 mg, 0.005 mmol, 0.1 eq) in dry acetonitrile (400 μl). The reaction is stirred for 2 h at room temperature, then water (100 μl) is added. The resulting solution is concentrated in vacuo. The residue is purified by basic reverse phase chromatography (gradient: H2O/acetonitrile/NH4OH from 50/50/0.1 to 20/80/0.1) to afford 9.4 mg of 1-[3-(2-{3-[6-(difluoromethoxy)pyridin-2-yl]pyrrolidin-1-yl}ethyl)pyridin-2-yl]piperidin-2-one 109.

Workup

  1. concentrationThe resulting solution is concentrated in vacuo
  2. customThe residue is purified by basic reverse phase chromatography (gradient: H2O/acetonitrile/NH4OH from 50/50/0.1 to 20/80/0.1)

Sources & evidence

ORD record
ord-30df3278c29c4c0ca038af2df56b2477
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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