Potassium Iodide → HCID 46832589, compound

HRID 1667755Notes

Reaction equation

HRID 1667755 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[N:14]=[CH:13][N:12]([C:15]3[S:16][C:17]([C:27]([NH2:29])=[O:28])=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=4)[N:19]=3)[C:11]=2[CH:30]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[NH:39]1[CH2:44][CH2:43]O[CH2:41][CH2:40]1.[CH3:45][N:46](C)C=O>>[Cl:26][C:22]1[CH:21]=[C:20]([C:18]2[N:19]=[C:15]([N:12]3[C:11]4[CH:30]=[C:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][N:39]5[CH2:44][CH2:43][N:46]([CH3:45])[CH2:41][CH2:40]5)[CH:8]=[CH:9][C:10]=4[N:14]=[CH:13]3)[S:16][C:17]=2[C:27]([NH2:29])=[O:28])[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 674446482-[6-(4-Chloro-butoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide

Product 1

HCID 46832589HCID 46832589, compound

Procedure

A mixture of 0.023 g (0.05 mmole) of 2-[6-(4-chloro-butoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (I.37a), 0.5 mL of dimethylformamide, 0.035 g (0.25 mmole) of potassium carbonate, 0.001 g of potassium iodide and 0.013 mL (0.15 mmole) of morpholine 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 0.019 g of 4-(3-chloro-phenyl)-2-{6-[4-(4-methyl-piperazin-1-yl)-butoxy]-benzoimidazol-1-yl}-thiazole-5-carboxylic acid amide (I.38) as a white powder. MH+/Z=512

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-d310a0f23641429b95a420d7ab39df13
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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