Acryloyl chloride → HCID 86713601, compound

HRID 524085Notes

Reaction equation

HRID 524085 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)=[O:22])[CH2:17][CH2:16]2)[C:12]([Cl:34])=[CH:11][N:10]=1.[C:35](Cl)(=[O:38])[CH:36]=[CH2:37].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:35]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[N:14]=[C:13]([N:15]2[CH2:16][CH2:17][N:18]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)=[O:22])[CH2:19][CH2:20]2)[C:12]([Cl:34])=[CH:11][N:10]=1)(=[O:38])[CH:36]=[CH2:37]

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 86713602HCID 86713602, compound

Product 1

HCID 86713601HCID 86713601, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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 crude reaction mixture
  2. custompurified

Sources & evidence

ORD record
ord-997580b3a856466f86c1073b65544068
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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