Triethylamine → HCID 15392199, compound

HRID 362502Notes

Reaction equation

HRID 362502 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:34]=[CH:33][C:18]([NH:19][CH2:20][C:21]3[CH:30]=[C:29]4[C:24]([CH:25]=[CH:26][C:27]([C:31]#[N:32])=[CH:28]4)=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:36](=[O:42])[C:37]([O:39][CH2:40][CH3:41])=[O:38].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([N:19]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]4[C:29](=[CH:28][C:27]([C:31]#[N:32])=[CH:26][CH:25]=4)[CH:30]=3)[C:36](=[O:42])[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:33][CH:34]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 20884Ethoxalyl chlorideHCID 15392197HCID 15392197, compound

Product 1

HCID 15392199HCID 15392199, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-[[4-[(1-t-Butoxycarbonyl-4-piperidyl)oxy]anilino]methyl]-2-naphthalenecarbonitrile obtained in Reference Example 2 (200 mg) was dissolved in 2 ml of dichloromethane, 299 mg of ethyl chloroglyoxylate and 266 mg of triethylamine were added to the solution, and the mixture was stirred at room temperature for 15 hours. Ethyl acetate was added to the reaction solution. The mixture was washed with 10% citric acid aqueous solution and saturated sodium bicarbonate aqueous solution in that order, dried over anhydrous sodium sulfate, and then evaporated. The resulting residue was purified by silica gel column chromatography using hexane:ethyl acetate (8:2) as the eluent to give 241 mg of ethyl N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-N-[(7-cyano-2-naphthyl)methyl]oxamate.

Workup

  1. washThe mixture was washed with 10% citric acid aqueous solution and saturated sodium bicarbonate aqueous solution in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated
  4. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-03e25298d35f4f90aa122357a15082e9
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

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