Trifluoroacetic acid → HCID 73056043, compound

HRID 1779109Notes

Reaction equation

HRID 1779109 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:48])[CH2:10][C:11]1[CH:47]=[CH:46][CH:45]=[CH:44][C:12]=1[CH2:13][CH2:14][C:15]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][N:18]=[C:17]([NH:25][C:26]2[CH:27]=[N:28][N:29]([CH:31]3[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]3)[CH:30]=2)[N:16]=1>C(Cl)Cl>[NH:34]1[CH2:33][CH2:32][CH:31]([N:29]2[CH:30]=[C:26]([NH:25][C:17]3[N:16]=[C:15]([CH2:14][CH2:13][C:12]4[CH:44]=[CH:45][CH:46]=[CH:47][C:11]=4[CH2:10][C:9]([NH2:8])=[O:48])[C:20]([C:21]([F:22])([F:24])[F:23])=[CH:19][N:18]=3)[CH:27]=[N:28]2)[CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712737HCID 86712737, compound

Product 1

HCID 73056043HCID 73056043, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2 mL) was added to a solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate (A137) (171 mg, 0.298 mmol) in DCM (25 mL) and the mixture was stirred at room temperature overnight. The volatiles were removed in vacuo and the resultant solid was dissolved in CHCl3 (1 mL). Cyclohexane (25 mL) was added and the resultant precipitate was removed by filtration, washed with cyclohexane (25 mL) and air dried to yield the title compound as a white solid (101 mg, 72%). LCMS-A: rt 4.717 min; m/z 474.2 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe resultant solid was dissolved in CHCl3 (1 mL)
  3. additionCyclohexane (25 mL) was added
  4. customthe resultant precipitate was removed by filtration
  5. washwashed with cyclohexane (25 mL) and air
  6. customdried

Sources & evidence

ORD record
ord-33ecd22b71704384bae1c77a7dbfec40
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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