Sodium Chloride → HCID 19964624, compound

HRID 233007Notes

Reaction equation

HRID 233007 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:17]([C:22]([OH:24])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[C:7]2[CH:25]=[C:26]([C:30]3[N:31]=[C:32]4[CH2:37][CH2:36][CH2:35][CH2:34][N:33]4[CH:38]=3)[CH:27]=[C:28]([CH3:29])[C:6]=2[N:5]=1)[CH2:2][CH3:3].[CH:39]1([O:45][C:46]([O:48][CH:49](I)[CH3:50])=[O:47])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>CS(C)=O>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([O:24][CH:49]([O:48][C:46]([O:45][CH:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)=[O:47])[CH3:50])=[O:23])=[CH:12][CH:11]=2)[C:7]2[CH:25]=[C:26]([C:30]3[N:31]=[C:32]4[CH2:37][CH2:36][CH2:35][CH2:34][N:33]4[CH:38]=3)[CH:27]=[C:28]([CH3:29])[C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 111092781-Iodoethyl cyclohexyl carbonateHCID 199645214'-[(2-n-Propyl-4-methyl-6-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-2-yl)-benzimidazol-1-yl)-methyl]-biphenyl-2-carboxylic acid

Product 1

HCID 19964624HCID 19964624, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 504 mg (1.0 mMol) of 4'-[(2-n-propyl-4-methyl-6-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-2-yl)-benzimidazol-1-yl)-methyl]-biphenyl-2-carboxylic acid, 600 mg of 1-(cyclohexyloxycarbonyloxy)-ethyliodide and 350 mg of potassium carbonate in 25 ml of dimethylsulphoxide is stirred for 14 hours at ambient temperature, then stirred into about 70 ml of saturated sodium chloride solution and extracted three times with 30 ml of ethyl acetate. The combined organic extracts are washed with water and evaporated down. The crude product thus obtained is purified by column chromatography (100 g silica gel; eluant: methylene chloride/ethanol=98:2).

Workup

  1. extractionextracted three times with 30 ml of ethyl acetate
  2. washThe combined organic extracts are washed with water
  3. customevaporated down

Sources & evidence

ORD record
ord-0d9473b9721c4004a1e152c3a2cf6995
Source dataset
uspto-grants-1997_01
Patent number
US05591762

Reaction notes

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