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Trifluoroacetic acid → 1-(2-(2-(2-((1-(Azetidin-3-yl)-1H-pyrazol-4-yl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

HRID 592388
Notes
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Reaction equation

HRID 592388 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:11]1([C:14]2[CH:45]=[CH:44][CH:43]=[CH:42][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[CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32]4)[CH:30]=3)[N:19]=2)[CH2:13][CH2:12]1)(=[O:10])[NH2:9]>C(Cl)Cl>[NH:33]1[CH2:32][CH:31]([N:29]2[CH:30]=[C:26]([NH:25][C:20]3[N:19]=[C:18]([CH2:17][CH2:16][C:15]4[CH:42]=[CH:43][CH:44]=[CH:45][C:14]=4[C:11]4([C:8]([NH2:9])=[O:10])[CH2:12][CH2:13]4)[C:23]([Cl:24])=[CH:22][N:21]=3)[CH:27]=[N:28]2)[CH2:34]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712299tert-Butyl 3-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)-1H-pyrazol-1-yl)azetidine-1-carboxylate

Product 1

HCID 732965761-(2-(2-(2-((1-(Azetidin-3-yl)-1H-pyrazol-4-yl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

TFA (1 mL) was added to a solution of tert-butyl 3-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)-1H-pyrazol-1-yl)azetidine-1-carboxylate A18 (0.110 g, 0.204 mmol) in DCM (5 mL) and the reaction was stirred for 16 hours. The volatiles were removed in vacuo and the resultant residue loaded onto an 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 and the solvent was removed in vacuo to give the title compound 14 as a tan solid (61 mg, 68%). 1H NMR (400 MHz, d4-MeOD) δ 8.27 (s, 1H), 8.09 (s, 1H), 7.65 (s, 1H), 7.44-7.37 (m, 2H), 7.34 (m, 1H), 7.27 (m, 1H), 5.36-5.18 (m, 1H), 4.15 (m, 2H), 3.96 (m, 2H), 3.20 (m, 4H), 1.63 (m, 2H), 1.20-1.05 (m, 2H). LCMS-C: rt 4.30 min; m/z 438.0 [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

Sources & evidence

ORD record
ord-1457b703f6c94a3f848df8e8c11966a7
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238644B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes