Water → Ethyl 3-(6-aminopyridin-3-yl)-2-{1-[(benzhydrylcarbamoyl)methyl]-1H-imidazol-4-yl}propionate

HRID 2370924Notes

Reaction equation

HRID 2370924 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][NH:18][CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].[CH:22]([NH:35][C:36](=[O:39])[CH2:37]Br)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][N:18]([CH2:37][C:36](=[O:39])[NH:35][CH:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 141859482-Bromo-N-(diphenylmethyl)acetamideHCID 178470993HCID 178470993, compound

Product 1

HCID 69331537Ethyl 3-(6-aminopyridin-3-yl)-2-{1-[(benzhydrylcarbamoyl)methyl]-1H-imidazol-4-yl}propionateYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 60.1 mg (0.23 mmol) of the compound from example 1g in 1 ml of absolute DMF was mixed with 11 mg (0.23 mmol) of sodium hydride (50%) and stirred at RT for 1 h. Then 70.3 mg (0.23 mmol) of the compound from example 10a were added, and the mixture was stirred at RT for 1 h. The reaction solution was mixed with 1 ml of water and extracted several times with EA. The combined EA extracts were dried over Na2SO4, filtered and concentrated. Purification of the resulting residue by chromatography on silica gel with CH2Cl2/methanol (9:1) as mobile phase afforded 71.4 mg of the title compound.

Workup

  1. stirringthe mixture was stirred at RT for 1 h
  2. extractionextracted several times with EA
  3. dry with materialThe combined EA extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the resulting residue by chromatography on silica gel with CH2Cl2/methanol (9:1) as mobile phase

Sources & evidence

ORD record
ord-9c841cbdad7f4de1ba1c240ee17021ed
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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