Sodium hydride → ethyl 3-(6-aminopyridin-3-yl)-2-{1-[2-(1-diphenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionate

HRID 2370935Notes

Reaction equation

HRID 2370935 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+].Br[CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31](=[O:45])[CH:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:27][CH2:26]1>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]([CH2:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31](=[O:45])[CH:32]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:27][CH2:26]3)[CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 674160211-[4-(2-Bromoethyl)piperidin-1-yl]-2,2-diphenylethanoneHCID 178470993HCID 178470993, compound

Product 1

HCID 67415723ethyl 3-(6-aminopyridin-3-yl)-2-{1-[2-(1-diphenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionateYield 31.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Ethyl 3-(6-aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propionate (100 mg; 0.38 mmol) was dissolved in absolute DMF (2 ml). Sodium hydride (50%; 19 mg; 0.38 mmol) was added, and the reaction mixture was stirred at RT for 1 h. Then 1-[4-(2-bromoethyl)piperidin-1-yl]-2,2-diphenylethanone (148 mg; 0.38 mmol) dissolved in absolute DMF (1 ml) was added. The reaction mixture was stirred at RT for 1 h and then concentrated under reduced pressure. The residue was taken up in 1N HCl and washed with dichlormethane (CH2Cl2; 2×). The aqueous phase was made basic with 1N NaOH and extracted with CH2Cl2 (3×). The combined organic phases were dried over Na2SO4. Removal of the solvent under reduced pressure resulted in ethyl 3-(6-aminopyridin-3-yl)-2-{1-[2-(1-diphenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionate (71 mg; 0.12 mmol).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at RT for 1 h
  3. concentrationconcentrated under reduced pressure
  4. washwashed with dichlormethane (CH2Cl2; 2×)
  5. extractionextracted with CH2Cl2 (3×)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-fd17600846c44e358be32055995a7a20
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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