N-bromobutanimide → HCID 117667006, compound

HRID 1526177Notes

Reaction equation

HRID 1526177 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].[Br:40]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:40][C:23]1[CH:22]=[C:21]([NH:20][C:5]2[C:4]([C:1](=[O:3])[NH2:2])=[N:9][CH:8]=[C:7]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)[N:6]=2)[CH:26]=[CH:25][C:24]=1[N:27]1[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 117667636HCID 117667636, compound

Product 1

HCID 117667006HCID 117667006, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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-bromosuccinimide (349 mg), followed by stirring at room temperature for 30 minutes. Then, N-bromosuccinimide (100 mg) was added thereto, followed by further stirring at room temperature for 30 minutes. 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-(2-bromo-4-{[3-carbamoyl-6-(3-nitrophenoxy)pyrazin-2-yl]amino}phenyl)piperazine-1-carboxylate (682 mg) as a yellow solid.

Workup

  1. stirringby further stirring at room temperature for 30 minutes
  2. additionTo the reaction mixture was added silica gel
  3. customthe solvent was evaporated under reduced pressure
  4. custompurified by silica gel column chromatography (eluent; chloroform)

Sources & evidence

ORD record
ord-3e07a11b1c864f61b7a9c71cbf46092b
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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