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

HRID 410904Notes

Reaction equation

HRID 410904 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][O:13][CH3:14])=[C:6]([NH2:15])[CH:5]=1.[NH2:17][C:18]1[S:19][C:20]2[CH:26]=[C:25]([O:27][C:28]([F:31])([F:30])[F:29])[CH:24]=[CH:23][C:21]=2[N:22]=1.[C:32](N1C=CN=C1)(N1C=CN=C1)=S.C(Cl)CCl>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][CH2:12][O:13][CH3:14])[C:32]([NH:17][C:18]3[S:19][C:20]4[CH:26]=[C:25]([O:27][C:28]([F:31])([F:29])[F:30])[CH:24]=[CH:23][C:21]=4[N:22]=3)=[N:15][C:6]=2[CH:5]=1)=[O:16]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 5070RiluzoleHCID 802641,1'-ThiocarbonyldiimidazoleHCID 50742440Methyl 3-amino-4-[(2-methoxyethyl)amino]benzoate

Product 1

HCID 866568491-(2-Methoxy-ethyl)-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl esterYield 49.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Methoxy-ethyl)-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester (829.0 mg) was prepared by following General Procedure D starting from 3-amino-4-(2-methoxy-ethylamino)-benzoic acid methyl ester (800.0 mg), 2-amino-6-(trifluoromethoxy)benzothiazole (930.0 mg), 1,1′-thiocarbonyldiimidazole (700.0 mg), and EDC (770.0 mg) in DMF (8.0 mL).

Sources & evidence

ORD record
ord-50d7d2dca69a48c8ba1c22431b63b526
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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