Riluzole → 1-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonitrile

HRID 410951Notes

Reaction equation

HRID 410951 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[NH:10][CH3:11].[NH2:12][C:13]1[S:14][C:15]2[CH:21]=[C:20]([O:22][C:23]([F:26])([F:25])[F:24])[CH:19]=[CH:18][C:16]=2[N:17]=1.[C:27](N1C=CN=C1)(N1C=CN=C1)=S>C(Cl)CCl>[CH3:27][N:1]1[C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[N:10]=[C:11]1[NH:12][C:13]1[S:14][C:15]2[CH:21]=[C:20]([O:22][C:23]([F:26])([F:24])[F:25])[CH:19]=[CH:18][C:16]=2[N:17]=1

Participants

5

Reactant 3

HCID 5070RiluzoleHCID 802641,1'-ThiocarbonyldiimidazoleHCID 110080674-Amino-3-(methylamino)benzonitrile

Product 1

HCID 583974971-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonitrile (2.27 g) was prepared by following General Procedure D starting from 4-amino-3-methylamino-benzonitrile (1.1 g), 2-amino-6-(trifluoromethoxy)benzothiazole (1.75 g), 1,1′-thiocarbonyldiimidazole (1.78 g), and EDC (1.9 g). This product was triturated with DCM-methanol (9:1) before being used in the next step.

Workup

  1. customThis product was triturated with DCM-methanol (9:1)

Sources & evidence

ORD record
ord-a563991e1d084e90b862fde3ec4df815
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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