Diisopropylcarbodiimide → 2-{2,6-Dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid methyl ester

HRID 1189688Notes

Reaction equation

HRID 1189688 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH:11][CH3:12])=[CH:6][C:5]=1[N:13]1[CH2:18][CH2:17][CH:16]([C:19]([F:22])([F:21])[F:20])[CH2:15][CH2:14]1.[Cl:24][C:25]1[C:38]([N:39]=[C:40]=S)=[C:37]([Cl:42])[CH:36]=[CH:35][C:26]=1[CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].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[CH2:18][CH2:17][CH:16]([C:19]([F:22])([F:20])[F:21])[CH2:15][CH2:14]2)=[CH:6][C:7]2[N:11]([CH3:12])[C:40]([NH:39][C:38]3[C:37]([Cl:42])=[CH:36][CH:35]=[C:26]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:25]=3[Cl:24])=[N:10][C:8]=2[CH:9]=1)=[O:23]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 56840192N-[(2,4-dichloro-3-isothiocyanatophenyl)methyl]-2,2-dimethylpropanamideHCID 67957313Methyl-2-[4-trifluoromethyl-piperidinyl]-4-methylamino-5-amino-benzoate

Product 1

HCID 679576072-{2,6-Dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The sub-title compound is prepared in analogy to 6c from methyl-2-[4-trifluoromethyl-piperidinyl]-4-methylamino-5-amino-benzoate (1.60 g, 4.82 mmol), and N-(2,4-dichloro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide (1.53 g, 4.82 mmol), DIC (0.82 mL, 5.3 mmol) and DMF (20 mL). Yield: 2.54 g. HPLC Rt=1.42 min (method A). MS m/z: 614 [M+H]+.

Sources & evidence

ORD record
ord-bcb4e874880047728af874a2d5f1ca43
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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