3-(Dimethylcarbamoyl)benzeneboronic acid → HCID 23654290, compound

HRID 1785519Notes

Reaction equation

HRID 1785519 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[N:12]=[CH:11]2)=[N:7][C:6]=1Br)=[O:4].[CH3:24][N:25]([CH3:37])[C:26]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)=[O:27]>>[CH3:20][O:19][C:17]1[C:16]([O:21][CH3:22])=[CH:15][C:14]2[N:10]([C:8]3[S:9][C:5]([C:3]([OH:2])=[O:4])=[C:6]([C:30]4[CH:31]=[CH:32][CH:33]=[C:28]([C:26](=[O:27])[N:25]([CH3:24])[CH3:37])[CH:29]=4)[N:7]=3)[CH:11]=[N:12][C:13]=2[CH:18]=1

Participants

3

Reactant 2

HCID 27733923-(Dimethylcarbamoyl)benzeneboronic acidHCID 57595851HCID 57595851, compound

Product 1

HCID 23654290HCID 23654290, compoundYield 4%

Procedure

In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-dimethylcarbamoylphenylboronic acid (29 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-dimethylcarbamoyl-phenyl)-thiazole-5-carboxylic acid (1.8 mg, 4%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.81 (s, 1 H); 7.84 (s, 1 H); 7.73-7.79 (m, 2H); 7.44-7.59 (m, 3 H); 7.40 (s, 1 H); 3.91 (s, 3 H, NCH3), 3.86 (s, 3 H); 3.01 (s, 3 H); 2.74 (s, 3 H). MS 453 m/z (M+1).

Sources & evidence

ORD record
ord-84897f4b243f4ede9a0f4e007c56cd65
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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