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Water → 4-(4-Fluorophenyl)-7-(morpholin-4-ylmethyl)quinoline-2-carboxamide

HRID 922770
Notes
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Reaction equation

HRID 922770 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:8][C:9]([C:13]#[N:14])=[N:10]2)=[CH:5][CH:4]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[OH-:28].[Na+].O>C(#N)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:7]2[C:6]3[C:11](=[CH:12][C:3]([CH2:2][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:4][CH:5]=3)[N:10]=[C:9]([C:13]([NH2:14])=[O:28])[CH:8]=2)=[CH:16][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 194270117-(Bromomethyl)-4-(4-fluorophenyl)quinoline-2-carbonitrile

Product 1

HCID 895451894-(4-Fluorophenyl)-7-(morpholin-4-ylmethyl)quinoline-2-carboxamideYield 89%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
50 °C

Procedure

To a room temperature solution of 7-(bromomethyl)-4-(4-fluorophenyl)quinoline-2-carbonitrile (2-1, 311.0 mg, 0.895 mmol, 1.0 equiv.) in acetonitrile (10.0 mL) was added morphline (85.77 mg, 0.985 mmol, 1.1 equiv.) and 5.0 M aqueous NaOH (2.69 mL, 13.43 mmol, 15 equiv.), and the resulting mixture was stirred at 50° C. for 4 days. After cooling to room temperature, water (100.0 mL) was added and the mixture was stirred for 30 minutes. A yellow solid was collected via suction filtration, washed with water, dried in vacuo. The solid was purified by reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA modifier) to afford 4-(4-fluorophenyl)-7-(morpholin-4-ylmethyl)quinoline-2-carboxamide (4-1, 291.0 mg, 80.0%) as a colorless solid. 1H NMR (500 MHz, CDCl3): δ 8.216 (s, 1H); 8.098 (br s, 2H); 7.911 (d, J=8.54 Hz, 1H); 7.642 (d, J=8.55 Hz, 1H); 7.503-7.529 (m, 2H); 7.219-7.263 (m, 2H); 5.798 (br s, 1H); 3.734 (br s, 6H); 2.528 (br s, 2H). LRMS m/z (M+H)+ 366.2 found, 366.2 required.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture was stirred for 30 minutes
  3. filtrationA yellow solid was collected via suction filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customThe solid was purified by reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA modifier)

Sources & evidence

ORD record
ord-f1b8ad40176646839dfd377f439b5813
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278960B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes