Triethylamine → N-[2-(2-azabicyclo[2.2.2]oct-2-yl)quinolin-6-yl]-N'-[4-(methylthio)phenyl]urea

HRID 6803

Reaction equation

HRID 6803 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][N:2]2[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:19])[CH:15]=2)[N:10]=1.C(N(CC)CC)C.[CH3:27][S:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=[O:37])=[CH:31][CH:30]=1>C(Cl)Cl>[CH:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH2:3][N:2]2[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH:19][C:36]([NH:35][C:32]3[CH:33]=[CH:34][C:29]([S:28][CH3:27])=[CH:30][CH:31]=3)=[O:37])[CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27333164-(Methylthio)phenyl isocyanateHCID 220189302-(2-Azabicyclo[2.2.2]oct-2-yl)quinolin-6-amine

Product 1

HCID 22018942N-[2-(2-azabicyclo[2.2.2]oct-2-yl)quinolin-6-yl]-N'-[4-(methylthio)phenyl]urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-azabicyclo[2.2.2]oct-2-yl)quinolin-6-amine (21 mg, 0.08 mmol, Example 119, Step B), triethylamine (0.013 mL, 0.09 mmol) in 1 mL methylene chloride was added 4-(methylthio)phenylisocyanate (15 mg, 0.09 mmol). The resulting mixture was stirred at r.t. for 2 h. The solvent was removed under vacuum and the residue was purified by preparative thin layer chromatography eluting with hexane/ethyl acetate (1:1) to afford the product, MS: m/z 419 (MH+), as an off-white solid.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by preparative thin layer chromatography
  3. washeluting with hexane/ethyl acetate (1:1)
  4. customto afford the product, MS

Sources & evidence

ORD record
ord-0e4d511f1a244853a580e3f8bc3bfe7d
Source dataset
uspto-grants-2006_08
Patent number
US07084156B2

Linked notes

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