Diisopropylcarbodiimide → N-(4-Bromo-phenyl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-fluoro-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 410105Notes

Reaction equation

HRID 410105 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:39])[C:10]2[CH:15]=[C:14]([NH:16][C:17]([NH:19][C:20]3[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:21]=3[Cl:35])=S)[C:13]([NH:36][CH3:37])=[CH:12][C:11]=2[F:38])=[CH:4][CH:3]=1.CC(C)N=C=NC(C)C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:10]2[C:11]([F:38])=[CH:12][C:13]3[N:36]([CH3:37])[C:17]([NH:19][C:20]4[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:21]=4[Cl:35])=[N:16][C:14]=3[CH:15]=2)=[O:39])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12734DiisopropylcarbodiimideHCID 86669631N-(4-Bromophenyl)-5-(3-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenyl}-thioureido)-2-fluoro-4-methylamino-benzamide

Product 1

HCID 56840186N-(4-Bromo-phenyl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-fluoro-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of crude N-(4-Bromophenyl)-5-(3-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenyl}-thioureido)-2-fluoro-4-methylamino-benzamide (400 mg), DIC (111 μl, 0.700 mmol) and DMF (5 mL) is stirred at 80° C. for 8 h. The crude mixture is concentrated and purified by flash chromatography (silica gel; DCM→DCM/EtOH 97:3) to give the title compound.

Workup

  1. concentrationThe crude mixture is concentrated
  2. custompurified by flash chromatography (silica gel; DCM→DCM/EtOH 97:3)

Sources & evidence

ORD record
ord-87170cd5bc9f4dd3a30101191dca79c3
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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