Hydrochloric Acid → N-(2,5-Di-4-morpholinyl-3-pyridinyl)-7-fluoro-2-(2-fluorophenyl)-3-methyl-4-quinolinamine

HRID 1431243Notes

Reaction equation

HRID 1431243 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:3]=1[CH3:20].[O:21]1[CH2:26][CH2:25][N:24]([C:27]2[C:32]([NH2:33])=[CH:31][C:30]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:29][N:28]=2)[CH2:23][CH2:22]1.Cl.O1CCOCC1>CO>[N:24]1([C:27]2[C:32]([NH:33][C:2]3[C:11]4[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=4)[N:5]=[C:4]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[F:19])[C:3]=3[CH3:20])=[CH:31][C:30]([N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)=[CH:29][N:28]=2)[CH2:23][CH2:22][O:21][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 596310462,5-Dimorpholinopyridin-3-amineHCID 596313954-Chloro-7-fluoro-2-(2-fluorophenyl)-3-methylquinoline

Product 1

HCID 50905718N-(2,5-Di-4-morpholinyl-3-pyridinyl)-7-fluoro-2-(2-fluorophenyl)-3-methyl-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to general Procedure K using 4-chloro-7-fluoro-2-(2-fluorophenyl)-3-methylquinoline (100 mg, 0.34 mmol), 2,5-dimorpholinopyridin-3-amine (91 mg, 0.34 mmol) and a 4.0M solution of HCl in dioxane (0.017 mL, 0.069 mmol) in MeOH (1.0 mL) and heating in the microwave for 2 h at 150° C. After purification N-(2,5-di-4-morpholinyl-3-pyridinyl)-7-fluoro-2-(2-fluorophenyl)-3-methyl-4-quinolinamine was obtained as a yellow film. 1H NMR (500 MHz, chloroform-d) δ ppm δ ppm 7.85 (1H, br. s.), 7.81 (1H, dd, J=9.9, 2.6 Hz), 7.58-7.65 (2H, m), 7.44-7.51 (1H, m), 7.30-7.37 (2H, m), 7.20 (1H, t, J=9.2 Hz), 6.85 (1H, br. s.), 6.27 (1H, br. s.), 3.94 (4H, t, J=4.6 Hz), 3.71-3.80 (4H, m), 3.22 (4H, br. s.), 2.98 (4H, br. s.), 2.18 (3H, s). Mass Spectrum (ESI) m/e=518.2 (M+1).

Workup

  1. customPrepared
  2. customAfter purification N-(2,5-di-4-morpholinyl-3-pyridinyl)-7-fluoro-2-(2-fluorophenyl)-3-methyl-4-quinolinamine
  3. customwas obtained as a yellow film

Sources & evidence

ORD record
ord-8afc291dff3e49069c85a37e302fac39
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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