Pyridine → HCID 9808440, compound

HRID 1585544Notes

Reaction equation

HRID 1585544 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@@H:11]2[CH2:16][N:15]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:14](=[O:25])[CH2:13][NH:12]2)=[CH:2]1.N1C=CC=CC=1.[F:32][C:33]([F:48])([F:47])[C:34]1[CH:35]=[C:36]([CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1)[C:37](Cl)=[O:38]>ClCCl>[F:32][C:33]([F:47])([F:48])[C:34]1[CH:35]=[C:36]([CH:40]=[C:41]([C:43]([F:46])([F:44])[F:45])[CH:42]=1)[C:37]([N:12]1[C@H:11]([CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:16][N:15]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:14](=[O:25])[CH2:13]1)=[O:38]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 10925957HCID 10925957, compound

Product 1

HCID 9808440HCID 9808440, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of (5R)-5-(1H-indol-3-ylmethyl)-1-[3-(ethoxycarbonyl)propyl]piperazin-2-one (0.56 g) and pyridine (0.26 ml) in dichloromethane (10 ml) was added a solution of 3,5-bis(trifluoromethyl)benzoyl chloride (0.45 g) in dichloromethane (1 ml). The solution was stirred for 40 minutes at the same temperature. After concentration, the residue was extracted with ethyl acetate. The organic layer was washed successively with aqueous sodium bicarbonate solution, water, 0.5N hydrochloric acid and brine, and dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (20 g) eluting with a mixture of dichloromethane-methanol (from 0% to 5% gradient solution) to give (5R)-4-[3,5-bis(trifluoromethyl)benzoyl]-1-[3-(ethoxycarbonyl)propyl]-5-(1H-indol-3-ylmethyl)piperazin-2-one (0.34 g) as an amorphous solid.

Workup

  1. concentrationAfter concentration
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer was washed successively with aqueous sodium bicarbonate solution, water, 0.5N hydrochloric acid and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (20 g)
  7. washeluting with a mixture of dichloromethane-methanol (from 0% to 5% gradient solution)

Sources & evidence

ORD record
ord-0fa86ada573a434cadfb1533ddb1b7cb
Source dataset
uspto-grants-1999_08
Patent number
US05939413

Reaction notes

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