Chlorosuccinimide → HCID 117675635, compound

HRID 1526213Notes

Reaction equation

HRID 1526213 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][C:7]([NH:28][C@@H:29]2[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30]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)=[C:13]([CH3:27])[CH:12]=1)(=[O:3])[NH2:2].[Cl:41]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[C:1]([C:4]1[N:5]=[C:6]([Cl:41])[C:7]([NH:28][C@@H:29]2[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30]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:21][CH2:22][CH2:23][O:24]3)[CH2:19][CH2:18]2)=[C:13]([CH3:27])[CH:12]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 117675614HCID 117675614, compound

Product 1

HCID 117675635HCID 117675635, compoundYield 69.1%

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)-3-methylphenyl]amino}pyrazin-2-yl)amino]pyrrolidine-1-carboxylate (1.16 g) and chloroform (35 mL) was added N-chlorosuccinimide (294 mg), followed by stirring at room temperature for 4 hours, and then N-chlorosuccinimide (84 mg) was added thereto, followed by stirring at room temperature for 1 hour. To the reactant was added silica gel, and then the solvent was evaporated under reduced pressure and then purified by silica gel column chromatography (eluent; chloroform) to obtain tert-butyl (3R)-3-[(5-carbamoyl-3-chloro-6-{[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-3-methylphenyl]amino}pyrazin-2-yl)amino]pyrrolidine-1-carboxylate (851 mg) as a yellow solid.

Workup

  1. stirringby stirring at room temperature for 1 hour
  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)

Sources & evidence

ORD record
ord-1d370c02acc646258cb88c87b9ae6ee6
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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