Trifluoroacetic acid → HCID 178495724, compound

HRID 20501Notes

Reaction equation

HRID 20501 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][O:9][CH2:10][C@H:11]([CH3:45])[O:12][C:13]1[CH:14]=[C:15]([CH:31]=[C:32]([O:34][C:35]2[CH:40]=[CH:39][C:38]([S:41]([CH3:44])(=[O:43])=[O:42])=[CH:37][CH:36]=2)[CH:33]=1)[C:16]([NH:18][C:19]1[CH:23]=[CH:22][N:21](C(OC(C)(C)C)=O)[N:20]=1)=[O:17]>C(Cl)Cl>[CH3:8][O:9][CH2:10][C@H:11]([CH3:45])[O:12][C:13]1[CH:14]=[C:15]([CH:31]=[C:32]([O:34][C:35]2[CH:36]=[CH:37][C:38]([S:41]([CH3:44])(=[O:42])=[O:43])=[CH:39][CH:40]=2)[CH:33]=1)[C:16]([NH:18][C:19]1[CH:23]=[CH:22][NH:21][N:20]=1)=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 59346881tert-butyl 3-({3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

Product 1

HCID 178495724HCID 178495724, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL) was added to a solution of tert-butyl 3-({3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate (180 mg, 0.330 mmol) in dry DCM (3 mL) and the reaction was stirred under argon for 3 h. A further portion of TFA (0.2 mL) was then added and the reaction was stirred for 30 min before all the solvent was removed in vacuo. The residue was taken up in ethyl acetate (30 mL) and saturated aqueous sodium hydrogencarbonate (15 mL) and the residue was evaporated then re-evaporated with DCM/hexanes to produce the title compound as a colourless foam (145 mg, 100%).

Workup

  1. stirringthe reaction was stirred for 30 min before all the solvent
  2. customwas removed in vacuo
  3. customsaturated aqueous sodium hydrogencarbonate (15 mL) and the residue was evaporated
  4. customthen re-evaporated with DCM/hexanes

Sources & evidence

ORD record
ord-380a12faceaa48269aaa84579aef6a9e
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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