Morpholine → 4-(3-Chloro-phenyl)-2-[6-(4-morpholin-4-yl-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester

HRID 1667766Notes

Reaction equation

HRID 1667766 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([CH2:20][CH2:21][CH2:22][CH2:23]OS(C)(=O)=O)[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([CH2:20][CH2:21][CH2:22][CH2:23][N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 866428384-(3-Chloro-phenyl)-2-[6-(4-methanesulfonyloxy-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 674437834-(3-Chloro-phenyl)-2-[6-(4-morpholin-4-yl-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl esterYield 74.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.107 g (0.2 mmole) of 4-(3-chloro-phenyl)-2-[6-(4-methanesulfonyloxy-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester (I.41e), 0.138 g (1 mmole) of potassium carbonate, 2 mL of acetonitrile and 0.035 mL (0.4 mmole) of morpholine was refluxed for 6 hours. The solid was removed by filtration and the filtrate concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane (gradient 0:100-5:95) to give 0.078 g of 4-(3-chloro-phenyl)-2-[6-(4-morpholin-4-yl-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester (I.41f) as a yellow solid.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe solid was removed by filtration
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with methanol-dichloromethane (gradient 0:100-5:95)

Sources & evidence

ORD record
ord-68ba802480f44ba7a75021c100a7c797
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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