Diisopropylcarbodiimide → 2-{2,6-Dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[3,3-difluoro-pyrrolidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid methyl ester

HRID 1189647Notes

Reaction equation

HRID 1189647 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH:11][CH3:12])=[CH:6][C:5]=1[N:13]1[CH2:17][CH2:16][C:15]([F:19])([F:18])[CH2:14]1.[Cl:21][C:22]1[C:35]([N:36]=[C:37]=S)=[C:34]([Cl:39])[CH:33]=[CH:32][C:23]=1[CH2:24][NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].CC(C)N=C=NC(C)C>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[C:5]([N:13]2[CH2:17][CH2:16][C:15]([F:19])([F:18])[CH2:14]2)=[CH:6][C:7]2[N:11]([CH3:12])[C:37]([NH:36][C:35]3[C:34]([Cl:39])=[CH:33][CH:32]=[C:23]([CH2:24][NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[C:22]=3[Cl:21])=[N:10][C:8]=2[CH:9]=1)=[O:20]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 56840192N-[(2,4-dichloro-3-isothiocyanatophenyl)methyl]-2,2-dimethylpropanamideHCID 67956984Methyl-2-[3,3-difluoro-pyrrolidinyl]-4-methylamino-5-amino-benzoate

Product 1

HCID 679572902-{2,6-Dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[3,3-difluoro-pyrrolidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared in analogy to 6c from methyl-2-[3,3-difluoro-pyrrolidinyl]-4-methylamino-5-amino-benzoate (1.19 g, 4.17 mmol), and N-(2,4-dichloro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide (1.32 g, 4.17 mmol), DIC (0.65 mL, 4.2 mmol) and DMF (20 mL).

Sources & evidence

ORD record
ord-29c70301e20b44a6882691efb0f18d99
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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