Riluzole → 1-Ethyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 410885Notes

Reaction equation

HRID 410885 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH3:12])=[C:6]([NH2:13])[CH:5]=1.[NH2:15][C:16]1[S:17][C:18]2[CH:24]=[C:23]([O:25][C:26]([F:29])([F:28])[F:27])[CH:22]=[CH:21][C:19]=2[N:20]=1.[C:30](N1C=CN=C1)(N1C=CN=C1)=S>C(Cl)CCl>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][CH3:12])[C:30]([NH:15][C:16]3[S:17][C:18]4[CH:24]=[C:23]([O:25][C:26]([F:29])([F:27])[F:28])[CH:22]=[CH:21][C:19]=4[N:20]=3)=[N:13][C:6]=2[CH:5]=1)=[O:14]

Participants

5

Reactant 3

HCID 5070RiluzoleHCID 802641,1'-ThiocarbonyldiimidazoleHCID 12758354Methyl 3-amino-4-(ethylamino)benzoate

Product 1

HCID 583976451-Ethyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl esterYield 54.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Ethyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester (3.70 g) was prepared by following General Procedure D starting from 3-amino-4-ethylamino-benzoic acid methyl ester (3.0 g), 2-amino-6-(trifluoromethoxy)benzothiazole (4.4 g), 1,1′-thiocarbonyldiimidazole (3.5 g), and EDC (3.6 g). LCMS: m/z 438; and 1H NMR (DMSO-d6, 400 MHz): δ 8.25 and 8.05 (0.59 and 0.53, 1H, m), 7.93 (2H, m), 7.75 (1H, m), 7.59 (1H, m), 7.38-7.37 (1H, m), 4.25-4.23 (2H, m), 3.88 (3H, s), 1.35-1.31 (3H, t), —NH proton signal was not observed.

Sources & evidence

ORD record
ord-4f9c82453a4140aea0a5614e151f05a1
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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