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Trifluoroacetic acid → 1-(2-(2-(5-Chloro-2-((6-(piperidin-4-yl)pyridin-3-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

HRID 592390
Notes
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Reaction equation

HRID 592390 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:11]1([C:14]2[CH:48]=[CH:47][CH:46]=[CH:45][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]=[CH:28][C:29]([CH:32]4[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]4)=[N:30][CH:31]=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:45]=[CH:46][CH:47]=[CH:48][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:31]=[N:30][C:29]([CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[CH:28][CH:27]=2)=[N:21][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712300tert-Butyl 4-(5-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino) pyridin-2-yl)piperidine-1-carboxylate

Product 1

HCID 732967111-(2-(2-(5-Chloro-2-((6-(piperidin-4-yl)pyridin-3-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of tert-butyl 4-(5-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate A19 (79.0 mg, 0.137 mmol) in DCM (5 mL) and 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 15 as a white solid (50 mg, 77%). 1H NMR (400 MHz, d4-MeOD) δ 8.74 (s, 1H), 8.36 (s, 1H), 8.21 (dd, J=8.6, 2.7 Hz, 1H), 7.45-7.22 (m, 5H), 3.30-3.17 (m, 6H), 2.95-2.80 (m, 3H), 1.99-1.96 (m, 2H), 1.86-1.76 (m, 2H), 1.64-1.63 (m, 2H), 1.19-1.07 (m, 2H). LCMS-C: rt 4.17 min; m/z 477.1 [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-882082ca25574441b76917badd4ab993
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