Trifluoroacetic acid → 1-(2-(2-(2-((4-(Piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)cyclobutanecarboxamide

HRID 592455Notes

Reaction equation

HRID 592455 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:11]1([C:15]2[CH:52]=[CH:51][CH:50]=[CH:49][C:16]=2[CH2:17][CH2:18][C:19]2[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][N:22]=[C:21]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([CH:36]4[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][CH2:37]4)=[CH:32][CH:31]=3)[N:20]=2)[CH2:14][CH2:13][CH2:12]1)(=[O:10])[NH2:9]>C(Cl)Cl>[NH:39]1[CH2:40][CH2:41][CH:36]([C:33]2[CH:32]=[CH:31][C:30]([NH:29][C:21]3[N:20]=[C:19]([CH2:18][CH2:17][C:16]4[CH:49]=[CH:50][CH:51]=[CH:52][C:15]=4[C:11]4([C:8]([NH2:9])=[O:10])[CH2:14][CH2:13][CH2:12]4)[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][N:22]=3)=[CH:35][CH:34]=2)[CH2:37][CH2:38]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712331tert-Butyl 4-(4-((4-(2-(1-carbamoylcyclobutyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Product 1

HCID 732951191-(2-(2-(2-((4-(Piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)cyclobutanecarboxamideYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of TFA (0.5 mL) and tert-butyl 4-(4-((4-(2-(1-carbamoylcyclobutyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate A57 (6.0 mg, 9.6 μL) in DCM (5 mL) was stirred at room temperature overnight. The volatiles were removed in vacuo before 2 M aq. NaOH (5 mL) was added to form a precipitate. The solid was collected by filtration and washed with cyclohexane (10 mL) to give the title compound 52 as a tan solid (1.5 mg, 30%). LCMS-A: rt 4.994 min; m/z 524.3 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo before 2 M aq. NaOH (5 mL)
  2. additionwas added
  3. customto form a precipitate
  4. filtrationThe solid was collected by filtration
  5. washwashed with cyclohexane (10 mL)

Sources & evidence

ORD record
ord-3459b6c30ff643e8a051cd1053e4f81b
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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