1,2-Dichloroethane → HCID 58397547, compound

HRID 410892Notes

Reaction equation

HRID 410892 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]([CH3:13])[CH3:12])=[C:6]([NH2:14])[CH:5]=1.[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>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH:11]([CH3:13])[CH3:12])[C:31]([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:14][C:6]=2[CH:5]=1)=[O:15]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 5070RiluzoleHCID 802641,1'-ThiocarbonyldiimidazoleHCID 2736795Methyl 3-Amino-4-(Isopropylamino)Benzoate

Product 1

HCID 58397547HCID 58397547, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Isopropyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester (580.0 mg) was prepared by following General Procedure D starting from 3-amino-4-isopropylamino-benzoic acid methyl ester (700.0 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). LCMS: m/z 452; and 1H NMR (DMSO-d6, 400 MHz): δ 8.27 and 8.05 (0.6 and 0.47, 1H, m), 7.93 (1H, m), 7.84 (1H, m), 7.73 (2H, m), 7.37 (1H, m), 5.15 (1H, m), 3.88 (3H, s), 1.58-1.57 (6H, d), —NH proton signal was not observed.

Sources & evidence

ORD record
ord-7abe069c1bfa4ed5adfaeacf613fd27b
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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