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

HRID 592392Notes

Reaction equation

HRID 592392 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:11]1([C:14]2[CH:47]=[CH:46][CH:45]=[CH:44][C:15]=2[CH2:16][CH2:17][C:18]2[C:23]([Cl:24])=[CH:22][N:21]=[C:20]([NH:25][C:26]3[CH:27]=[N:28][N:29]([CH:31]4[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]4)[CH:30]=3)[N:19]=2)[CH2:13][CH2:12]1)(=[O:10])[NH2:9]>C(Cl)Cl>[Cl:24][C:23]1[C:18]([CH2:17][CH2:16][C:15]2[CH:44]=[CH:45][CH:46]=[CH:47][C:14]=2[C:11]2([C:8]([NH2:9])=[O:10])[CH2:13][CH2:12]2)=[N:19][C:20]([NH:25][C:26]2[CH:27]=[N:28][N:29]([CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[CH:30]=2)=[N:21][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712301tert-Butyl 4-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 732967121-(2-(2-(5-Chloro-2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamideYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of tert-butyl 4-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate A20 (0.021 g, 0.037 mmol) in DCM (5 mL) and the mixture was stirred for 16 hours. The volatiles were removed in vacuo and the resultant residue loaded onto a SCX cartridge (5 g). The cartridge was washed with MeOH (100 mL) and then with 5% NH4OH in MeOH (100 mL). The basic fractions were combined, the solvent was removed in vacuo and the resultant residue purified by prep-LCMS to give the title compound 17 as a yellow solid (3.6 mg, 21%). LCMS-B: rt 4.711 min; m/z 466.2 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. washThe cartridge was washed with MeOH (100 mL)
  3. customthe solvent was removed in vacuo
  4. customthe resultant residue purified by prep-LCMS

Sources & evidence

ORD record
ord-91cf6715484d4f1a84ead442c674d9b0
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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