Water → HCID 18542567, compound

HRID 1268191Notes

Reaction equation

HRID 1268191 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22]/[CH:23]=[CH:24]/[C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=3)[C:28]#[N:29])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:39](OC(=O)C)(=[O:41])[CH3:40].O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:22]/[CH:23]=[CH:24]/[C:25]3[CH:32]=[CH:31][CH:30]=[C:27]([C:28]#[N:29])[CH:26]=3)[C:39](=[O:41])[CH3:40])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 18542676HCID 18542676, compound

Product 1

HCID 18542567HCID 18542567, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-[N-[4-(1-t-butoxycarbonylpiperidin-4-yloxy)phenyl]amino]-1-(E)-propenyl]benzonitrile (503 mg) and pyridine (0.14 ml) in dichloromethane (10 ml) was added acetic anhydride (0.13 ml) in an ice bath. The mixture was stirred at room temperature for 1 hour. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=1/1→ethyl acetate as an eluant to afford yellow crystals. The crystals were washed with diisopropyl ether to give the desired compound (403 mg, yield 50%) as pale yellow crystals.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was purified by chromatography on a silica gel column
  7. customto afford yellow crystals
  8. washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-8e1b9d0ddbeb4d17be95610604887741
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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