Piperazine → HCID 90051736, compound

HRID 2284689Notes

Reaction equation

HRID 2284689 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([N:7]([C@@H:9]([CH3:42])[C:10]([NH:12][C:13]1[CH:14]=[C:15]([NH:19][C:20]([C:22]2[C:23]([NH:38][CH2:39][CH2:40][CH3:41])=[N:24][C:25]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([C:35](=[O:37])[NH2:36])=[CH:31][CH:30]=3)=[N:26][CH:27]=2)=[O:21])[CH:16]=[CH:17][CH:18]=1)=[O:11])[CH3:8])=[O:6].[NH:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>CN(C)C=O>[C:35]([C:32]1[CH:33]=[CH:34][C:29]([NH:28][C:25]2[N:24]=[C:23]([NH:38][CH2:39][CH2:40][CH3:41])[C:22]([C:20]([NH:19][C:15]3[CH:16]=[CH:17][CH:18]=[C:13]([NH:12][C:10](=[O:11])[C@@H:9]([N:7]([CH3:8])[C:5](=[O:6])/[CH:4]=[CH:3]/[CH2:2][N:43]4[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]4)[CH3:42])[CH:14]=3)=[O:21])=[CH:27][N:26]=2)=[CH:30][CH:31]=1)(=[O:37])[NH2:36]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 90051737HCID 90051737, compound

Product 1

HCID 90051736HCID 90051736, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S,E)-N-(3-(2-(4-bromo-N-methyl-2-butenamido)propanamido)phenyl)-2-((4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxamide (3-7, 100 mg) in N,N-dimethylformamide (2 mL), piperazine (135 mg) was added at room temperature, and the mixture was stirred at the same temperature for 1 hour and 40 minutes. The solvent was evaporated under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (eluent, 85% ethyl acetate/15% methanol) to obtain (S,E)-2-((4-carbamoylphenyl)amino)-N-(3-(2-(N-methyl-4-(piperazin-1-yl)-2-butenamido)propanamido)phenyl)-4-(propylamino)pyrimidine-5-carboxamide (4-1, 57 mg) as white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained residue was purified by basic silica gel column chromatography (eluent, 85% ethyl acetate/15% methanol)

Sources & evidence

ORD record
ord-288b854f44914b57b5f2f7fa6ded7015
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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