Potassium Iodide → HCID 46832591, compound

HRID 1667751

Reaction equation

HRID 1667751 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(=O)([O-])[O-].[K+].[K+].[I-].[K+].[OH:38][CH2:39][CH2:40][NH:41][CH2:42][CH2:43][OH:44]>CN(C)C=O>[OH:38][CH2:39][CH2:40][N:41]([CH2:42][CH2:43][OH:44])[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

6

Reactant 4

HCID 4875Potassium IodideHCID 8113DiethanolamineHCID 11430Potassium CarbonateHCID 674272962-[6-(3-Chloro-propoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide

Product 1

HCID 46832591HCID 46832591, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 0.029 mL (0.3 mmole) of 2-(2-hydroxy-ethylamino)-ethanol was stirred at 100 degrees for 3 hours. The mixture was concentrated under reduced pressure, and diluted with 20 mL of water. The precipitate was collected by filtration and the solid triturated with diethyl ether to give 0.029 g of 2-(6-{3-[bis-(2-hydroxy-ethyl)-amino]-propoxy}-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (I.35) as a white powder. MH+/Z=516

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with 20 mL of water
  3. filtrationThe precipitate was collected by filtration
  4. customthe solid triturated with diethyl ether

Sources & evidence

ORD record
ord-2063aee5b7894deb9ec8494200923fb0
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Linked notes

Loading…