Trifluoroacetic acid → 1-(2-(2-(2-((4-(1-Aminoethyl)phenyl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

HRID 592403Notes

Reaction equation

HRID 592403 reaction equation
[C:1]([C:4]1([C:7]2[CH:38]=[CH:37][CH:36]=[CH:35][C:8]=2[CH2:9][CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH:25]([NH:27]C(=O)OC(C)(C)C)[CH3:26])=[CH:21][CH:20]=3)[N:12]=2)[CH2:6][CH2:5]1)(=[O:3])[NH2:2].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:27][CH:25]([C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:13]2[N:12]=[C:11]([CH2:10][CH2:9][C:8]3[CH:35]=[CH:36][CH:37]=[CH:38][C:7]=3[C:4]3([C:1]([NH2:2])=[O:3])[CH2:5][CH2:6]3)[C:16]([Cl:17])=[CH:15][N:14]=2)=[CH:24][CH:23]=1)[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 73296872tert-Butyl (1-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)phenyl)ethyl)carbamate

Product 1

HCID 867123031-(2-(2-(2-((4-(1-Aminoethyl)phenyl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamideYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)phenyl)ethyl)carbamate 24 (0.012 g, 0.022 mmol) in DCM (1 mL) was added trifluoroacetic acid (0.5 mL). The mixture was stirred at ambient temperature for 2 hours before the volatiles were removed in vacuo. The crude residue was loaded onto an SCX cartridge conditioned with methanol. The cartridge was washed with methanol and then 2 N ammonia in ethanol. The basic fractions were combined and the solvent removed in vacuo to give the title compound 24A as a colourless oil (0.009 g, 92%). LCMS-C: rt 4.41 min; m/z 436 [M+H]+.

Workup

  1. customwere removed in vacuo
  2. washThe cartridge was washed with methanol
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3c96f7942432498786a0803eaca01506
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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