Trifluoroacetic acid → HCID 73055745, compound

HRID 1779074Notes

Reaction equation

HRID 1779074 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:53])[CH2:10][C:11]1[CH:48]=[C:47]([C:49]([F:52])([F:51])[F:50])[CH:46]=[CH:45][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:31]=[CH:30][C:29]([CH:32]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)=[CH:28][CH:27]=2)[N:16]=1>C(Cl)Cl>[NH:35]1[CH2:36][CH2:37][CH:32]([C:29]2[CH:30]=[CH:31][C:26]([NH:25][C:17]3[N:16]=[C:15]([CH2:14][CH2:13][C:12]4[CH:45]=[CH:46][C:47]([C:49]([F:50])([F:51])[F:52])=[CH:48][C:11]=4[CH2:10][C:9]([NH2:8])=[O:53])[C:20]([C:21]([F:24])([F:22])[F:23])=[CH:19][N:18]=3)=[CH:27][CH:28]=2)[CH2:33][CH2:34]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712715HCID 86712715, compound

Product 1

HCID 73055745HCID 73055745, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1.0 mL) was added to a solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)-4-(trifluoromethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A109) (0.121 g, 0.185 mmol) in DCM (10 mL) and the resulting mixture stirred for 24 hours at room temperature. The volatiles were evaporated under reduced pressure and the residue was dissolved in DCM. Cyclohexane was added and the resultant precipitate was collected by vacuum filtration to give the title compound 25 as a cream solid (0.065 g, 68%); 1H NMR (400 MHz, d4-MeOH) δ 8.55 (s, 1H), 7.61 (d, J=8.5 Hz, 2H), 7.57 (s, 1H), 7.50 (d, J=8.3 Hz, 1H), 7.39 (d, J=8.1 Hz, 1H), 7.22 (d, J=8.6 Hz, 2H), 4.73-4.49 (m, 2H), 3.74 (s, 2H), 3.28-3.21 (m, 2H), 3.17-3.09 (m, 2H), 2.95 (m, 2H), 2.84-2.71 (m, 1H), 1.96 (d, J=13.6 Hz, 2H), 1.79 (m, 2H). LCMS-A: rt 4.679 min; m/z 552.3 [M+H]+.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in DCM
  3. additionCyclohexane was added
  4. filtrationthe resultant precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-60241b7a30554a878b93f89d2df4fa55
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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