Trifluoroacetic acid → HCID 69933247, compound

HRID 540797Notes

Reaction equation

HRID 540797 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:38]=[CH:37][C:6]([O:7][C:8]2[N:12]([CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[N:11]=[C:10]([C:19]3[CH:20]=[C:21]([C:25]4([NH:29]C(=O)OC(C)(C)C)[CH2:28][O:27][CH2:26]4)[CH:22]=[CH:23][CH:24]=3)[CH:9]=2)=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:29][C:25]1([C:21]2[CH:20]=[C:19]([C:10]3[CH:9]=[C:8]([O:7][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:39])[F:40])=[CH:38][CH:37]=4)[N:12]([CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[N:11]=3)[CH:24]=[CH:23][CH:22]=2)[CH2:28][O:27][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69932959HCID 69932959, compound

Product 1

HCID 69933247HCID 69933247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of tert-butyl [3-(3-{5-(4-trifluoromethylphenoxy)-1-[2-(dimethylamino)-2-oxoethyl]-1H-pyrazol-3-yl}phenyl)oxetan-3-yl]carbamate (70 mg, 0.13 mmol) in 2 mL of CH2Cl2 was cooled in an ice bath. To the solution was added 1 mL of TFA and the mixture was stirred for 1 h. The cooling bath was removed and the mixture was stirred at ambient temperature for 1 h. 10% Aqueous Na2CO3 solution was added and the mixture was extracted with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give 2-{3-[3-(3-aminooxetan-3-yl)phenyl]-5-(4-trifluoromethylphenoxy)-1H-pyrazol-1-yl}-N,N-dimethylacetamide as an oil. Calcd (M+1)+: 461.4. Found: 461.5

Workup

  1. customThe cooling bath was removed
  2. stirringthe mixture was stirred at ambient temperature for 1 h
  3. addition10% Aqueous Na2CO3 solution was added
  4. extractionthe mixture was extracted with CH2Cl2
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6c29bf2ee8734986b24e5f3af6db96b8
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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