Ethanolamine → HCID 46832591, compound

HRID 1667752Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[CH:12][N:11]([C:14]3[S:15][C:16]([C:26]([NH2:28])=[O:27])=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=4)[N:18]=3)[C:10]=2[CH:29]=1.[C:30](=[O:33])([O-])[O-].[K+].[K+].[I-].[K+].[NH2:38][CH2:39][CH2:40][OH:41].[CH3:42]N(C)C=O>>[OH:41][CH2:40][CH2:39][N:38]([CH2:42][CH2:30][OH:33])[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[CH:12][N:11]([C:14]3[S:15][C:16]([C:26]([NH2:28])=[O:27])=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=4)[N:18]=3)[C:10]=2[CH:29]=1

Participants

Reactant 5

HCID 700Ethanolamine

HCID 4875Potassium Iodide

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 674272962-[6-(3-Chloro-propoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide

Product 1

HCID 46832591HCID 46832591, compound

Procedure

A mixture of 0.043 g (0.1 mmole) of 2-[6-(3-chloro-propoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (I.34a), 1 mL of dimethylformamide, 0.069 g (0.5 mmole) of potassium carbonate, 0.001 g of potassium iodide and 0.011 mL (0.2 mmole) of 2-amino-ethanol was stirred at 100 degrees for 6 hours. The mixture was cooled, the solid was removed by filtration and the filtrate purified by reverse phase silica gel chromatography, eluting with acetonitrile-water (gradient 20:80-100:0) to give 0.031 g of 2-(6-{3-[bis-(2-hydroxy-ethyl)-amino]-propoxy}-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (I.36) as a white powder. MH+/Z=472

Workup

temperatureThe mixture was cooled
customthe solid was removed by filtration
customthe filtrate purified by reverse phase silica gel chromatography
washeluting with acetonitrile-water (gradient 20:80-100:0)

Sources & evidence

ORD record: ord-9ff9b612bff14f85835cc84617ec5b79
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044213B2

Reaction notes

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