N-bromobutanimide → HCID 117675688, compound

HRID 1526219Notes

Reaction equation

HRID 1526219 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][C:7]([NH:27][C@@H:28]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29]2)=[N:8][C:9]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:26][CH2:25][C:20]3([O:24][CH2:23][CH2:22][O:21]3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)(=[O:3])[NH2:2].[Br:40]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:40][C:6]1[C:7]([NH:27][C@@H:28]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29]2)=[N:8][C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:18][CH2:19][C:20]4([O:21][CH2:22][CH2:23][O:24]4)[CH2:25][CH2:26]3)=[CH:13][CH:12]=2)=[C:4]([C:1](=[O:3])[NH2:2])[N:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 117675686HCID 117675686, compound

Product 1

HCID 117675688HCID 117675688, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of tert-butyl (3R)-3-[(5-carbamoyl-6-{[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]amino}pyrazin-2-yl)amino]pyrrolidine-1-carboxylate (10 g), chloroform (200 mL) was added N-bromosuccinimide (3.46 g) under ice-cooling, followed by stirring for 1 hour. To the reactant was added silica gel, and the solvent was evaporated under reduced pressure and then purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-400:10:1) to obtain tert-butyl (3R)-3-[(3-bromo-5-carbamoyl-6-{[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]amino}pyrazin-2-yl)amino]pyrrolidine-1-carboxylate (6.17 g) as a yellow amorphous substance.

Workup

  1. temperaturecooling
  2. additionTo the reactant was added silica gel
  3. customthe solvent was evaporated under reduced pressure
  4. custompurified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-400:10:1)

Sources & evidence

ORD record
ord-be3f6df812fa43a99a1fbe01d7fcbe2a
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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