Acetonitrile → HCID 15392212, compound

HRID 362514Notes

Reaction equation

HRID 362514 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].[CH2:35]([S:37]N=C=O)C.[C:41](#[N:43])[CH3:42]>>[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:35]([NH:43][CH2:41][CH3:42])=[S:37])=[CH:33][CH:34]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 15392197HCID 15392197, compoundHCID 21933416HCID 21933416, compound

Product 1

HCID 15392212HCID 15392212, compound

Procedure

7-[[4-[(1-t-Butoxycarbonyl-4-piperidyl)oxy]anilino]methyl]-2-naphthalenecarbonitrile obtained in Reference Example 2 (150 mg) was dissolved in 4 ml of acetonitrile, 710 mg of ethyl thioisocyanate was added to the solution, and the mixture was heated under reflux for 4 days. The reaction solution was evaporated, and the resulting residue was purified by silica gel column chromatography using hexane:ethyl acetate (7:3) as the eluent to give 171 mg of 1-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-1-[(7-cyano-2-naphthyl)methyl]-3-ethylthiourea.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 days
  3. customThe reaction solution was evaporated
  4. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c6ae5e9471194b45bdbed991c3a8e546
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

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