1,2-Dichloroethane → 3-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-3H-benzoimidazole-5-carboxylic acid ethyl ester

HRID 411002Notes

Reaction equation

HRID 411002 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([NH2:11])[S:10][C:6]=2[CH:5]=1.[CH2:16]([O:18][C:19](=[O:29])[C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([NH:27][CH3:28])[CH:21]=1)[CH3:17].[CH2:30](Cl)CCl>CN(C=O)C>[CH2:16]([O:18][C:19]([C:20]1[CH:25]=[CH:24][C:23]2[N:26]=[C:28]([NH:11][C:9]3[S:10][C:6]4[CH:5]=[C:4]([O:3][C:2]([F:1])([F:14])[F:15])[CH:13]=[CH:12][C:7]=4[N:8]=3)[N:27]([CH3:30])[C:22]=2[CH:21]=1)=[O:29])[CH3:17]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5070RiluzoleHCID 67332734Ethyl 4-amino-3-(methylamino)benzoate

Product 1

HCID 866569143-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-3H-benzoimidazole-5-carboxylic acid ethyl esterYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-3H-benzoimidazole-5-carboxylic acid ethyl ester (2.8 g) was prepared by following General Procedure D starting from 6-trifluoromethoxy-benzothiazol-2-ylamine (2.9 g), 4-amino-3-methylamino-benzoic acid ethyl ester (2.1 g), thioCDI (2.2 g) and EDC (2.4 g) in DMF (30 mL).

Sources & evidence

ORD record
ord-364389f468544c70b06ef5a47430da9c
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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