Trifluoroacetic acid → 1-(2-(2-(5-Methyl-2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

HRID 592438Notes

Reaction equation

HRID 592438 reaction equation
[C:1]([C:4]1([C:7]2[CH:40]=[CH:39][CH:38]=[CH:37][C:8]=2[CH2:9][CH2:10][C:11]2[C:16]([CH3:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]3[CH:20]=[N:21][N:22]([CH:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)[CH:23]=3)[N:12]=2)[CH2:6][CH2:5]1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:17][C:16]1[C:11]([CH2:10][CH2:9][C:8]2[CH:37]=[CH:38][CH:39]=[CH:40][C:7]=2[C:4]2([C:1]([NH2:2])=[O:3])[CH2:5][CH2:6]2)=[N:12][C:13]([NH:18][C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:23]=2)=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712317tert-Butyl 4-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 867123181-(2-(2-(5-Methyl-2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate A43 (0.113 g, 0.207 mmol) in DCM (10 mL) was treated with TFA (0.32 mL, 4.1 mmol) and stirred for 20 hours at room temperature. The volatiles were evaporated in vacuo and aq. NaOH (2 M, 40 mL) was added to the residue. The aqueous phase was extracted with EtOAc (3×40 mL) and the combined organics were washed with brine and dried over MgSO4. The solvent was removed in vacuo and the solid was suspended in DCM. Cyclohexane was added and the suspension was sonicated for 10 minutes. The solid was isolated by vacuum filtration to give the title compound A44 as an off-white solid (0.066 g, 72%). LCMS-D: rt 2.88 min; m/z 446 [M+H]+.

Workup

  1. customThe volatiles were evaporated in vacuo and aq. NaOH (2 M, 40 mL)
  2. additionwas added to the residue
  3. extractionThe aqueous phase was extracted with EtOAc (3×40 mL)
  4. washthe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. additionCyclohexane was added
  8. customthe suspension was sonicated for 10 minutes
  9. customThe solid was isolated by vacuum filtration

Sources & evidence

ORD record
ord-86ae2a06c5fe4eb59e0b0baab1f57442
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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