Trifluoroacetic acid → HCID 86713601, compound

HRID 2404067Notes

Reaction equation

HRID 2404067 reaction equation
C(O[C:6](=[O:41])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]2[CH2:26][CH2:25][N:24]([C:27](=[O:39])[NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=3)[CH2:23][CH2:22]2)[C:18]([Cl:40])=[CH:17][N:16]=1)(C)(C)C.[C:42](O)([C:44](F)(F)F)=O.NC1C=CC=CC=1NC1N=C(N2CCN(C(NC3C=CC=C(C(F)(F)F)C=3)=O)CC2)C(Cl)=CN=1.C(Cl)(=O)C=C.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:6]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]2[CH2:22][CH2:23][N:24]([C:27]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:37])([F:38])[F:36])[CH:30]=3)=[O:39])[CH2:25][CH2:26]2)[C:18]([Cl:40])=[CH:17][N:16]=1)(=[O:41])[CH:42]=[CH2:44]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 86713600HCID 86713600, compoundHCID 86713602HCID 86713602, compound

Product 1

HCID 86713601HCID 86713601, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl(2-((5-chloro-4-(4-((3-(trifluoromethyl)phenyl)carbamoyl)piperazin-1-yl)pyrimidin-2-yl)amino)phenyl)carbamate (0.025 g, 0.043 mmol) in DCM (1.0 mL) was added TFA (1.0 mL) and the mixture was stirred for 1 h. An aliquot of the reaction mixture was analyzed by LCMS, which indicated that the reaction had proceeded to completion. The solvents were removed and the residue was dried on high vacuum. The crude product was used for the next step without further purification. To a solution of 4-(2-((2-aminophenyl)amino)-5-chloropyrimidin-4-yl)-N-(3-(trifluoromethyl)phenyl)piperazine-1-carboxamide (0.043 mmol) in DCM (0.5 mL) was added acryloyl chloride (0.004 mL, 0.052 mmol) and DIEA (0.018 mL, 0.11 mmol) and the mixture was stirred at 0° C. for 1 h. The crude reaction mixture was loaded onto silica gel and purified using 0-7% MeOH/DCM gradient to give the title compound (10 mg, 43%). MS (ES+) C25H23ClF3N7O2 requires: 545. found: 546 [M+H]+

Workup

  1. customThe solvents were removed
  2. customthe residue was dried on high vacuum
  3. customThe crude product was used for the next step without further purification
  4. stirringthe mixture was stirred at 0° C. for 1 h
  5. customThe crude reaction mixture
  6. custompurified

Sources & evidence

ORD record
ord-2228a8c5a7ba43ee992a456a7a96e8f0
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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