Diisopropylcarbodiimide → N-(3,3,3-Trifluoropropyl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[3-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 1189665Notes

Reaction equation

HRID 1189665 reaction equation
[F:1][C:2]([F:28])([F:27])[CH2:3][CH2:4][NH:5][C:6](=[O:26])[C:7]1[CH:12]=[C:11]([NH2:13])[C:10]([NH:14][CH3:15])=[CH:9][C:8]=1[N:16]1[CH2:21][CH2:20][CH2:19][CH:18]([C:22]([F:25])([F:24])[F:23])[CH2:17]1.[Cl:29][C:30]1[C:43]([N:44]=[C:45]=S)=[C:42]([Cl:47])[CH:41]=[CH:40][C:31]=1[CH2:32][NH:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36].CC(C)N=C=NC(C)C>CC#N>[F:28][C:2]([F:1])([F:27])[CH2:3][CH2:4][NH:5][C:6]([C:7]1[C:8]([N:16]2[CH2:21][CH2:20][CH2:19][CH:18]([C:22]([F:23])([F:24])[F:25])[CH2:17]2)=[CH:9][C:10]2[N:14]([CH3:15])[C:45]([NH:44][C:43]3[C:42]([Cl:47])=[CH:41][CH:40]=[C:31]([CH2:32][NH:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[C:30]=3[Cl:29])=[N:13][C:11]=2[CH:12]=1)=[O:26]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 56840192N-[(2,4-dichloro-3-isothiocyanatophenyl)methyl]-2,2-dimethylpropanamideHCID 86666473N-(3,3,3-Trifluoro-propyl)-2-[3-trifluoromethyl-piperidinyl]-4-methylamino-5-amino-benzoic acid amide

Product 1

HCID 86666475N-(3,3,3-Trifluoropropyl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[3-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound is prepared in analogy to 6c from N-(3,3,3-trifluoro-propyl)-2-[3-trifluoromethyl-piperidinyl]-4-methylamino-5-amino-benzoic acid amide (93 mg, 0.22 mmol), and N-(2,4-dichloro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide (71 mg, 0.22 mmol), DIC (35 μL) and MeCN (2.0 mL).

Sources & evidence

ORD record
ord-eaf60e1811e240058dc75ff9d6321fa3
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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