1,1'-Thiocarbonyldiimidazole → 2-(5-fluoro-benzothiazol-2-ylamino)-1-methyl-1H-benzimidazole-5-carboxylic acid methyl ester

HRID 410838Notes

Reaction equation

HRID 410838 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH3:11])=[C:6]([NH2:12])[CH:5]=1.[NH2:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:18]=2[N:19]=1.[C:25](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]([CH3:25])[C:11]([NH:14][C:15]3[S:16][C:17]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:18]=4[N:19]=3)=[N:12][C:6]=2[CH:5]=1)=[O:13]

Participants

5

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 8212032-Amino-5-fluorobenzothiazoleHCID 15586064Methyl 3-amino-4-(methylamino)benzoate

Product 1

HCID 583974762-(5-fluoro-benzothiazol-2-ylamino)-1-methyl-1H-benzimidazole-5-carboxylic acid methyl esterYield 65.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Methyl-2-(5-fluoro-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester (1.16 g) was prepared by following General Procedure D starting from 3-amino-4-methylamino-benzoic acid methyl ester (0.9 g), 2-amino-5-fluoro-benzothiazole (0.84 g), 1,1′-thiocarbonyldiimidazole (1.07 g), and EDC (1.15 g). LC/MS: m/z 358.

Sources & evidence

ORD record
ord-5b5582110d80472f9a246c69343d1c3f
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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