Riluzole → HCID 58397693, compound

HRID 410786Notes

Reaction equation

HRID 410786 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH:11][CH3:12])=[CH:6][C:5]=1[O:13][CH3:14].[NH2:16][C:17]1[S:18][C:19]2[CH:25]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:20]=2[N:21]=1.[C:31](N1C=CN=C1)(N1C=CN=C1)=S>C(Cl)CCl>[CH3:1][O:2][C:3]([C:4]1[C:5]([O:13][CH3:14])=[CH:6][C:7]2[N:11]([CH3:31])[C:12]([NH:16][C:17]3[S:18][C:19]4[CH:25]=[C:24]([O:26][C:27]([F:30])([F:28])[F:29])[CH:23]=[CH:22][C:20]=4[N:21]=3)=[N:10][C:8]=2[CH:9]=1)=[O:15]

Participants

5

Reactant 3

HCID 5070RiluzoleHCID 802641,1'-ThiocarbonyldiimidazoleHCID 67230618HCID 67230618, compound

Product 1

HCID 58397693HCID 58397693, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-Methoxy-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester (80 mg) was prepared by following General Procedure D starting from 5-amino-2-methoxy-4-methylamino-benzoic acid methyl ester (95 mg), 2-amino-6-(trifluoromethoxy)benzothiazole (82 mg), 1,1′-thiocarbonyldiimidazole (90 mg), and EDC (108 mg). LC/MS: m/z 453.8. 1H NMR (DMSO-d6, 400 MHz): δ 12.24, (s, 1H), 7.97 (s, 1H), 7.92 (s, 1H), 7.71 (d, 1H), 7.36 (d, 1H), 7.24 (s, 1H), 3.90 (s, 3H), 3.80 (s, 3H), 3.64 (s, 3H).

Sources & evidence

ORD record
ord-8bd6e877762a465496c433d29d044b7b
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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