Trifluoroacetic acid → HCID 178461788, compound

HRID 1990279Notes

Reaction equation

HRID 1990279 reaction equation
FC(F)(F)C(O)=O.[N:8]1([C:12]([C:14]2[N:15]=[CH:16][C:17]([O:20][C:21]3[CH:22]=[C:23]([C:35]([NH:37][C:38]4[CH:42]=[CH:41][N:40](C(OC(C)(C)C)=O)[N:39]=4)=[O:36])[CH:24]=[C:25]([O:27][C@@H:28]([CH3:34])[CH2:29][O:30][CH:31]([F:33])[F:32])[CH:26]=3)=[N:18][CH:19]=2)=[O:13])[CH2:11][CH2:10][CH2:9]1>C(Cl)Cl>[N:8]1([C:12]([C:14]2[N:15]=[CH:16][C:17]([O:20][C:21]3[CH:22]=[C:23]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:34])[CH2:29][O:30][CH:31]([F:33])[F:32])[CH:26]=3)[C:35]([NH:37][C:38]3[CH:42]=[CH:41][NH:40][N:39]=3)=[O:36])=[N:18][CH:19]=2)=[O:13])[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 591271291,1-dimethylethyl 3-({[3-{[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-({(1S)-2-[(difluoromethyl)oxy]-1-methylethyl}oxy)phenyl]carbonyl}amino)-1H-pyrazole-1-carboxylate

Product 1

HCID 178461788HCID 178461788, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of 1,1-dimethylethyl 3-({[3-{[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-({(1S)-2-[(difluoromethyl)oxy]-1-methylethyl}oxy)phenyl]carbonyl}amino)-1H-pyrazole-1-carboxylate (115 mg, 0.17 mmol) in DCM (16 mL) and stirred at RT for 2 hours. The solvent was removed in vacuo, DCM (20 mL) added and the mixture washed with water (20 mL), a saturated solution of sodium bicarbonate (20 mL), brine (20 mL), dried (MgSO4), filtered and reduced in vacuo to give the desired compound as a white foam (93 mg).

Workup

  1. customThe solvent was removed in vacuo, DCM (20 mL)
  2. additionadded
  3. washthe mixture washed with water (20 mL)
  4. dry with materiala saturated solution of sodium bicarbonate (20 mL), brine (20 mL), dried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c7cf10247c624ecca57368b0fc230b82
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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