Trifluoroacetic acid → HCID 57659786, compound

HRID 1011619Notes

Reaction equation

HRID 1011619 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:39])[C:9]2[C:13]([CH2:14][N:15]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)(=[O:25])=[O:24])C(=O)OC(C)(C)C)=[CH:12][N:11]([CH2:36][O:37][CH3:38])[N:10]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:39])[C:9]2[C:13]([CH2:14][NH:15][S:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)(=[O:24])=[O:25])=[CH:12][N:11]([CH2:36][O:37][CH3:38])[N:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57659776HCID 57659776, compound

Product 1

HCID 57659786HCID 57659786, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (3-((4-fluorophenyl)(hydroxy)methyl)-1-(methoxymethyl)-1H-pyrazol-4-yl)methyl(4-(trifluoromethyl)phenylsulfonyl)carbamate (44) (434 mg, 0.757 mmol) was dissolved in CH2Cl2 (4 mL) and stirred at rt under nitrogen. Trifluoroacetic acid (4 mL) was added and the reaction stirred for 1 hr before concentration in vacuo. The resulting crude product was purified by column chromatography using EtOAc/hexane gradients to yield N-((3-((4-fluorophenyl)(hydroxy)methyl)-1-(methoxymethyl)-1H-pyrazol-4-yl)methyl)-4-(trifluoromethyl)benzenesulfonamide (45) (120 mg, 35%) as a white solid.

Workup

  1. stirringthe reaction stirred for 1 hr before concentration in vacuo
  2. customThe resulting crude product was purified by column chromatography

Sources & evidence

ORD record
ord-16caac2cd60d406fa0436594f2ab86d2
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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