Trifluoroacetic acid → 1-(2-(2-(2-(4-(1-Aminoethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

HRID 592494Notes

Reaction equation

HRID 592494 reaction equation
[C:1]([C:4]1([C:7]2[CH:41]=[CH:40][CH:39]=[CH:38][C:8]=2[CH2:9][CH2:10][C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][N:14]=[C:13]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH:28]([NH:30]C(=O)OC(C)(C)C)[CH3:29])=[CH:24][CH:23]=3)[N:12]=2)[CH2:6][CH2:5]1)(=[O:3])[NH2:2].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:30][CH:28]([C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:13]2[N:12]=[C:11]([CH2:10][CH2:9][C:8]3[CH:38]=[CH:39][CH:40]=[CH:41][C:7]=3[C:4]3([C:1]([NH2:2])=[O:3])[CH2:5][CH2:6]3)[C:16]([C:17]([F:19])([F:20])[F:18])=[CH:15][N:14]=2)=[CH:27][CH:26]=1)[CH3:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 73295800tert-Butyl 1-(4-(4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)ethylcarbamate

Product 1

HCID 867123501-(2-(2-(2-(4-(1-Aminoethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamideYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-(4-(4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)ethylcarbamate 70 (0.11 g, 0.19 mmol) in DCM (4 mL) was added trifluoroacetic acid (2 mL). The mixture was stirred at ambient temperature for 16 hours before the volatiles were removed in vacuo. The crude residue was purified using an SCX conditioned with MeOH, product was eluted off with 2 M ammonia in EtOH) to give the title compound 70A as a cream solid (0.073 g, 81%). LCMS-C: rt 4.48 min; m/z 470 [M+H]+.

Workup

  1. customwere removed in vacuo
  2. customThe crude residue was purified
  3. washwas eluted off with 2 M ammonia in EtOH)

Sources & evidence

ORD record
ord-4fe429c53cb64e7182bc121bce42c63e
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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