2,5-Dimethoxytetrahydrofuran → HCID 66913834, compound

HRID 2104529Notes

Reaction equation

HRID 2104529 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1.CO[CH:32]1[CH2:36][CH2:35][CH:34](OC)O1>C(O)(=O)C>[C:24]1([C:22]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:8]=2[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([N:1]4[CH:32]=[CH:36][CH:35]=[CH:34]4)[CH:3]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:18]([F:21])([F:19])[F:20])=[O:23])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 11326798[4-(3-Aminophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

Product 1

HCID 66913834HCID 66913834, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of [4-(3-aminophenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (0.04 g, 0.1 mmol) and 2,5-dimethoxytetrahydrofuran (0.08 g, 0.6 mmol) in 5 mL of acetic acid was heated at 80 for 1 h. Removal of solvent under reduced pressure gave a crude product that was purified by silica gel chromatography eluting with ethyl acetate/hexanes (5% to 30%) to give 30 mg (67%) of the title compound as an off-white solid. MS (ESI) m/z 443; HRMS: calcd for C27H17F3N2O, 442.1293; found (ESI, [M+H]+), 443.1373.

Workup

  1. temperaturewas heated at 80 for 1 h
  2. customRemoval of solvent under reduced pressure
  3. customgave a crude product that
  4. customwas purified by silica gel chromatography
  5. washeluting with ethyl acetate/hexanes (5% to 30%)

Sources & evidence

ORD record
ord-19418a4d6d55423b94c0347eed59d3b6
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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