Chlorosuccinimide → HCID 117666920, compound

HRID 1526178Notes

Reaction equation

[C:1]([C:4]1[C:5]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)=[N:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)=[CH:8][N:9]=1)(=[O:3])[NH2:2].[Cl:40]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[C:1]([C:4]1[C:5]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([N:27]3[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:32]3)=[C:25]([Cl:40])[CH:26]=2)=[N:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)=[CH:8][N:9]=1)(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of tert-butyl 4-(4-{[3-carbamoyl-6-(3-nitrophenoxy)pyrazin-2-yl]amino}phenyl)piperazine-1-carboxylate (1 g) and chloroform (30 mL) was added N-chlorosuccinimide (262 mg), and the reaction mixture was stirred at 50° C. for 15 hours and further, at 60° C. for 24 hours. To the reaction mixture was added silica gel, and the solvent was evaporated under reduced pressure and then purified by silica gel column chromatography (eluent; chloroform) to obtain tert-butyl 4-(4-{[3-carbamoyl-6-(3-nitrophenoxy)pyrazin-2-yl]amino}-2-chlorophenyl)piperazine-1-carboxylate (1.05 g) as a yellow solid.

Workup

waitfurther, at 60° C. for 24 hours
additionTo the reaction mixture was added silica gel
customthe solvent was evaporated under reduced pressure
custompurified by silica gel column chromatography (eluent; chloroform)

Sources & evidence

ORD record: ord-81f522d128fc40808ce39f84e2b85d75
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085540B2

Reaction notes

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