Hydrochloric Acid → 2-((2-(2-Fluorophenyl)-3-methyl-4-quinolinyl)amino)-4-(4-morpholinyl)-benzonitrile

HRID 1431291Notes

Reaction equation

HRID 1431291 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[C:18]=1[CH3:34].Cl.O1CCOCC1>CN1C(=O)CCC1>[F:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:19]1[C:18]([CH3:34])=[C:17]([NH:1][C:2]2[CH:9]=[C:8]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 134992832-Amino-4-(4-morpholinyl)benzonitrileHCID 596311684-Chloro-2-(2-fluorophenyl)-3-methylquinoline

Product 1

HCID 509061352-((2-(2-Fluorophenyl)-3-methyl-4-quinolinyl)amino)-4-(4-morpholinyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Prepared according to Procedure K, Method 2 using 2-amino-4-morpholinobenzonitrile (82 mg, 405 μmol), 4-chloro-2-(2-fluorophenyl)-3-methylquinoline (110 mg, 405 μmol) and 4N hydrochloric acid solution in dioxane (0.010 mL, 40 μmol) in NMP (0.50 mL) to afford product as a tan solid upon purification by chromatography on silica gel, eluting with EtOAc gradient in DCM. 1H NMR (400 MHz, chloroform-d) δ ppm 8.11 (1H, d, J=8.6 Hz), 7.90 (1H, d, J=8.6 Hz), 7.61-7.74 (1H, m), 7.45-7.61 (2H, m), 7.32-7.45 (2H, m), 7.26 (1H, t, J=7.4 Hz), 7.08 (1H, t, J=9.2 Hz), 6.55 (1H, br. s.), 6.31 (1H, dd, J=8.8, 2.5 Hz), 5.76 (1H, br. s.), 3.54-3.73 (4H, m), 2.88-3.11 (4H, m), 2.04-2.23 (3H, m). Mass Spectrum (ESI) m/e=439.1 (M+1).

Workup

  1. customPrepared
  2. customto afford product as a tan solid
  3. customupon purification by chromatography on silica gel
  4. washeluting with EtOAc gradient in DCM

Sources & evidence

ORD record
ord-adb0d99e709a46b8a6cd0639f1460828
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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