Water → N-{3-[2-(Acetylamino)ethyl]-4-hydroxy-2,3-dihydro-1H-inden-5-yl}-5-pyridin-2-ylpentanamide

HRID 340698Notes

Reaction equation

HRID 340698 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O.S(Cl)(Cl)=O.Cl.[NH2:19][C:20]1[C:28]([OH:29])=[C:27]2[C:23]([CH2:24][CH2:25][CH:26]2[CH2:30][CH2:31][NH:32][C:33](=[O:35])[CH3:34])=[CH:22][CH:21]=1.O>N1C=CC=CC=1.C(OCC)(=O)C>[C:33]([NH:32][CH2:31][CH2:30][CH:26]1[C:27]2[C:23](=[CH:22][CH:21]=[C:20]([NH:19][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:28]=2[OH:29])[CH2:24][CH2:25]1)(=[O:35])[CH3:34]

Participants

7

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 112523245-pyridin-2-ylpentanoic AcidHCID 67354374N-[2-(6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide Hydrochloride

Product 1

HCID 57781225N-{3-[2-(Acetylamino)ethyl]-4-hydroxy-2,3-dihydro-1H-inden-5-yl}-5-pyridin-2-ylpentanamideYield 26%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5-pyridin-2-ylpentanoic acid (72.8 mg, 0.406 mmol) was added thionyl chloride (0.4 mL), and the mixture was heated under reflux for 30 min. Thionyl chloride was evaporated under reduced pressure and the residue was diluted with pyridine (2 mL). The mixture was added to a solution of N-[2-(6-amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide hydrochloride (100 mg, 0.369 mmol) in pyridine (2 mL) under ice-cooling, and the mixture was stirred for 15 min. Water was added, and the mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10) to give the title compound (37.7 mg, yield 26%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. customThionyl chloride was evaporated under reduced pressure
  4. additionthe residue was diluted with pyridine (2 mL)
  5. temperaturecooling
  6. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10)

Sources & evidence

ORD record
ord-059586e782894604bfb38d5f4426f20a
Source dataset
uspto-grants-2014_11
Patent number
US08895591B2

Reaction notes

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