2,2-Difluoro-2-(fluorosulfonyl)acetic acid → HCID 178508984, compound

HRID 2042838Notes

Reaction equation

HRID 2042838 reaction equation
[F:1][C:2]([F:10])(S(F)(=O)=O)C(O)=O.[F:11][C:12]([F:37])([F:36])[C@H:13]1[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:35])[C:21]2[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[C:24]([NH2:30])=[N:23][C:22]=2[O:31][CH2:32][CH2:33][OH:34])[CH2:15][CH2:14]1>CC#N.[Cu]I>[F:37][C:12]([F:36])([F:11])[C@H:13]1[CH2:14][CH2:15][C@H:16]([NH:19][C:20](=[O:35])[C:21]2[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[C:24]([NH2:30])=[N:23][C:22]=2[O:31][CH2:32][CH2:33][O:34][CH:2]([F:10])[F:1])[CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 178508983HCID 178508983, compound

Product 1

HCID 178508984HCID 178508984, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent2×

Procedure

2,2-Difluoro-2-fluorosulfonylacetic acid (205 μl, 1.98 mmol) in MeCN (20 ml) is added via a syringe pump to a mixture of N-(trans-4-trifluoromethyl-cyclohexyl)-2-(2-hydroxy-ethoxy)-6-amino-5-nitro-nicotinamide (390 mg, 0.994 mmol) and CuI (94 mg, 0.49 mmol) in MeCN (40 ml) over 2.5 h at 55° C. It is stirred for additional 20 min, then the mixture is concentrated and purified via extensive chromatography.

Workup

  1. concentrationthe mixture is concentrated
  2. custompurified via extensive chromatography

Sources & evidence

ORD record
ord-b7a297a27a75435f822bd888c9a61d96
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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