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1,1'-Thiocarbonyldiimidazole → 2-(6-Methanesulfonyl-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 410844
Notes
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Reaction equation

HRID 410844 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]=[C:22]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=[CH:20][C:18]=2[N:19]=1.[C:28](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]([CH3:28])[C:11]([NH:14][C:15]3[S:16][C:17]4[CH:23]=[C:22]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=[CH:20][C:18]=4[N:19]=3)=[N:12][C:6]=2[CH:5]=1)=[O:13]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 871522-Benzothiazolamine, 6-(methylsulfonyl)-HCID 15586064Methyl 3-amino-4-(methylamino)benzoate

Product 1

HCID 583975832-(6-Methanesulfonyl-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carboxylic acid methyl esterYield 78.9%

Reagents, catalysts & solvents 1

HCID 11
1,2-Dichloroethane
Solvent

Procedure

2-(6-Methanesulfonyl-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carboxylic acid methyl ester (1.64 g) was prepared by following General Procedure D starting from 3-amino-4-methylamino-benzoic acid methyl ester (0.9 g), 2-amino-6-methanesulfonyl-benzothiazole (1.14 g), 1,1′-thiocarbonyldiimidazole (1.07 g), and EDC (1.15 g). LC/MS: m/z 418.

Sources & evidence

ORD record
ord-ce39c1b176cc4314aaf33a9cce5cd659
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08759535B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes