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

HRID 1431244Notes

Reaction equation

HRID 1431244 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:3]=1[CH3:19].[O:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:31]([NH2:32])=[CH:30][C:29]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:28][N:27]=2)[CH2:22][CH2:21]1.Cl.O1CCOCC1>CO>[N:23]1([C:26]2[C:31]([NH:32][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][C:10]=4[F:12])[N:5]=[C:4]([C:13]4[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=4)[C:3]=3[CH3:19])=[CH:30][C:29]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[CH:28][N:27]=2)[CH2:22][CH2:21][O:20][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 596310462,5-Dimorpholinopyridin-3-amineHCID 596315274-Chloro-5-fluoro-3-methyl-2-(pyridin-3-yl)quinoline

Product 1

HCID 50905280N-(2,5-Di-4-morpholinyl-3-pyridinyl)-5-fluoro-3-methyl-2-(3-pyridinyl)-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to general Procedure K using 4-chloro-5-fluoro-3-methyl-2-(pyridin-3-yl)quinoline (83 mg, 0.30 mmol), 2,5-dimorpholinopyridin-3-amine (80 mg, 0.30 mmol) and a 4.0M solution of HCl in dioxane (0.015 mL, 0.061 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)-5-fluoro-3-methyl-2-(3-pyridinyl)-4-quinolinamine was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.87 (1H, d, J=2.3 Hz), 8.73 (1H, dd, J=4.9, 1.8 Hz), 7.93-8.03 (2H, m), 7.84 (1H, d, J=12.1 Hz), 7.66 (1H, d, J=2.7 Hz), 7.59-7.64 (1H, m), 7.49 (1H, dd, J=7.8, 5.1 Hz), 7.16-7.24 (1H, m), 6.37 (1H, d, J=2.7 Hz), 3.87-3.98 (4H, m), 3.75-3.86 (4H, m), 3.22 (4H, br. s.), 2.95-3.07 (4H, m), 2.19 (3H, s). Mass Spectrum (ESI) m/e=501.2 (M+1).

Workup

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

Sources & evidence

ORD record
ord-64a573051d2346f1947b58832c86c997
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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