Chlorosuccinimide → HCID 86700509, compound

HRID 1500520Notes

Reaction equation

HRID 1500520 reaction equation
[CH3:1][O:2][C:3](=[O:29])[NH:4][C@H:5]([C:9]([N:11]1[CH2:15][C@@H:14]([CH3:16])[CH2:13][C@H:12]1[C:17]1[NH:18][CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)[N:21]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].[Cl:30]N1C(=O)CCC1=O>C(#N)C>[CH3:1][O:2][C:3](=[O:29])[NH:4][C@H:5]([C:9]([N:11]1[CH2:15][C@@H:14]([CH3:16])[CH2:13][C@H:12]1[C:17]1[NH:18][C:19]([Cl:30])=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)[N:21]=1)=[O:10])[CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178502437HCID 178502437, compound

Product 1

HCID 86700509HCID 86700509, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ((S)-1-{(2S,4S)-2-[4-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-methyl-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (175 mg, 0.38 mmol) and N-chlorosuccinimide (202 mg, 1.51 mmol) in acetonitrile (4 mL) was stirred at RT overnight. The reaction mixture was concentrated by rotary evaporation and purified by silica gel chromatography (24 g silica, 0-100% hexanes/EtOAc) to provide the title intermediate (208 mg) as a brown solid. (m/z): [M+H]+ calcd for C21H2BrClN4O3 497.09, found 497.4.

Workup

  1. concentrationThe reaction mixture was concentrated by rotary evaporation
  2. custompurified by silica gel chromatography (24 g silica, 0-100% hexanes/EtOAc)

Sources & evidence

ORD record
ord-9199b798c3d9404888db81d0ce149c9d
Source dataset
uspto-grants-2015_12
Patent number
US09206159B2

Reaction notes

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