Riluzole → 6-Fluoro-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid (2-methoxy-ethyl)-amide

HRID 410764Notes

Reaction equation

HRID 410764 reaction equation
[NH2:1][C:2]1[C:3]([NH:16][CH3:17])=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([NH:9][CH2:10][CH2:11][O:12][CH3:13])=[O:8].[NH2:18][C:19]1[S:20][C:21]2[CH:27]=[C:26]([O:28][C:29]([F:32])([F:31])[F:30])[CH:25]=[CH:24][C:22]=2[N:23]=1.[C:33](N1C=CN=C1)(N1C=CN=C1)=S>C(Cl)CCl>[CH3:13][O:12][CH2:11][CH2:10][NH:9][C:7]([C:6]1[C:5]([F:15])=[CH:4][C:3]2[N:16]([CH3:33])[C:17]([NH:18][C:19]3[S:20][C:21]4[CH:27]=[C:26]([O:28][C:29]([F:32])([F:30])[F:31])[CH:25]=[CH:24][C:22]=4[N:23]=3)=[N:1][C:2]=2[CH:14]=1)=[O:8]

Participants

5

Reactant 3

HCID 5070RiluzoleHCID 802641,1'-ThiocarbonyldiimidazoleHCID 673333195-Amino-2-fluoro-N-(2-methoxy-ethyl)-4-methylamino-benzamide

Product 1

HCID 866567736-Fluoro-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid (2-methoxy-ethyl)-amideYield 33.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-Fluoro-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid (2-methoxy-ethyl)-amide (41 mg) was prepared by following General Procedure D starting from 5-amino-2-fluoro-N-(2-methoxy-ethyl)-4-methylamino-benzamide (72 mg), 2-amino-6-(trifluoromethoxy)-benzothiazole (59 mg), 1,1′-thiocarbonyldiimidazole (64 mg), and EDC (77 mg). LC/MS: m/z 484.8. 1H NMR (DMSO-d6, 400 MHz): δ 12.35 (bs, 1H), 8.16 (s, 1H), 7.91 (d, 1H), 7.88 (s, 1H), 7.73 (d, 1H), 7.50 (d, 1H), 7.36 (d, 1H), 3.61 (bs, 3H), 3.51-3.40 (m, 4H), 3.30 (s, 3H).

Sources & evidence

ORD record
ord-2b7c7b118b7b47f591f0450cab1e5f80
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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