1,1'-Thiocarbonyldiimidazole → HCID 53356441, compound

HRID 410752Notes

Reaction equation

HRID 410752 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]([F:24])[C:21]([F:25])=[CH:20][C:18]=2[N:19]=1.[C:26](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]([CH3:26])[C:11]([NH:14][C:15]3[S:16][C:17]4[CH:23]=[C:22]([F:24])[C:21]([F:25])=[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 150505592-Amino-5,6-difluorobenzothiazoleHCID 15586064Methyl 3-amino-4-(methylamino)benzoate

Product 1

HCID 53356441HCID 53356441, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-(5,6-Difluoro-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carboxylic acid methyl ester (579 mg) was prepared by following General Procedure D starting from 3-amino-4-methylamino-benzoic acid methyl ester (650 mg), 2-amino-5,6-difluorobenzothiazole (560 mg), 1,1′-thiocarbonyldiimidazole (715 mg), and EDC (865 mg). LC/MS: m/z 375.8. 1H NMR (DMSO-d6, 400 MHz): δ 12.51 (bs, 1H), 8.25 (s, 1H), 8.19 (s, 1H), 7.85 (s, 1H), 7.68 (d, 1H), 7.52 (d, 1H), 3.86 (s, 3H), 3.67 (bs, 3H).

Sources & evidence

ORD record
ord-e7e54be62204496a8509cc7bb6c9b68c
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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