Diisopropylcarbodiimide → Ethyl 2-(2-chloro-5-{[(tert.butylcarbonyl)amino]methyl}phenylamino)-6-(2,2-difluoroethoxy)-1-methyl-1H-benzo[d]imidazole-5-carboxylate

HRID 1410259Notes

Reaction equation

HRID 1410259 reaction equation
[F:1][CH:2]([F:19])[CH2:3][O:4][C:5]1[CH:15]=[C:14]([NH:16][CH3:17])[C:13]([NH2:18])=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:20][C:21]1[CH:34]=[CH:33][C:24]([CH2:25][NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:23][C:22]=1[N:35]=[C:36]=S.CC(C)N=C=NC(C)C>CN(C=O)C>[Cl:20][C:21]1[CH:34]=[CH:33][C:24]([CH2:25][NH:26][C:27]([C:28]([CH3:31])([CH3:30])[CH3:29])=[O:32])=[CH:23][C:22]=1[NH:35][C:36]1[N:16]([CH3:17])[C:14]2[CH:15]=[C:5]([O:4][CH2:3][CH:2]([F:1])[F:19])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12][C:13]=2[N:18]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 59529827Ethyl 2-(2,2-difluoroethoxy)-4-methylamino-5-amino-benzoateHCID 86646343HCID 86646343, compound

Product 1

HCID 59529856Ethyl 2-(2-chloro-5-{[(tert.butylcarbonyl)amino]methyl}phenylamino)-6-(2,2-difluoroethoxy)-1-methyl-1H-benzo[d]imidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The sub-title compound was prepared from ethyl 2-(2,2-difluoroethoxy)-4-methylamino-5-amino-benzoate and N-(4-chloro-3-isothiocyanatobenzyl)-2,2-dimethylpropionamide with DIC in DMF at r.t. in analogy to example 72a. The crude material was directly used in the next step.

Sources & evidence

ORD record
ord-afbcff8857064843915688c3a6ac2719
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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