Ethylamine → 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethylamide

HRID 1785486Notes

Reaction equation

HRID 1785486 reaction equation
C(O[C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([O:22][CH3:23])[C:18]([O:20][CH3:21])=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:5])C.[CH2:30]([NH2:32])[CH3:31]>CO>[CH2:30]([NH:32][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([O:22][CH3:23])[C:18]([O:20][CH3:21])=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:5])[CH3:31]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 24886662HCID 24886662, compound

Product 1

HCID 236544692-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethylamide was prepared from 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (30 mg, 0.07 mmol) and ethylamine in methanol (2 molar) as described above in the general amide formation procedure. Product was isolated by preparative HPLC: 16 mg, 56%. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.81 (s, 1H); 8.53 (t, 1H); 7.88-7.69 (m, 3H); 7.55-7.44 (m, 3H); 7.40 (s, 1H); 3.88 (s, 3H); 3.85 (s, 3H); 3.25 (q, 2H); 1.08 (t, 3H). MS M/z 409 (M+1).

Workup

  1. customProduct was isolated by preparative HPLC

Sources & evidence

ORD record
ord-bab919471b49460297e5e432b8cbb56a
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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