Trifluoroacetic acid → HCID 73056320, compound

HRID 1779113Notes

Reaction equation

HRID 1779113 reaction equation
[NH2:1][C:2](=[O:36])[CH2:3][C:4]1[CH:35]=[CH:34][CH:33]=[CH:32][C:5]=1[CH2:6][CH2:7][C:8]1[C:13]([Cl:14])=[CH:12][N:11]=[C:10]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([NH:24]C(=O)OC(C)(C)C)[CH3:23])=[CH:18][CH:17]=2)[N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH3:1].[NH2:24][CH:22]([C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:10]2[N:9]=[C:8]([CH2:7][CH2:6][C:5]3[CH:32]=[CH:33][CH:34]=[CH:35][C:4]=3[CH2:3][C:2]([NH2:1])=[O:36])[C:13]([Cl:14])=[CH:12][N:11]=2)=[CH:21][CH:20]=1)[CH3:23]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712741HCID 86712741, compound

Product 2

HCID 222AmmoniaHCID 73056320HCID 73056320, compoundYield 174.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-(4-(4-(2-(2-amino-2-oxoethyl)phenethyl)-5-chloropyrimidin-2-ylamino)phenyl)ethylcarbamate (A140) (0.0070 g, 0.014 mmol) in DCM (1 mL) was added TFA (0.50 mL). The mixture was stirred at ambient temperature for 2 hours before the volatiles were removed in vacuo. The crude residue was purified using an SCX cartridge, (MeOH then 2 N ammonia in EtOH eluent) to give the title compound (37) as a grey solid (0.005 g, 89%). LCMS-C: rt 4.29 min; m/z 410 [M+H]+

Workup

  1. customwere removed in vacuo
  2. customThe crude residue was purified

Sources & evidence

ORD record
ord-21a1c23e2057494db457c6f43cf8b0c4
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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