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

HRID 1431383Notes

Reaction equation

HRID 1431383 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]([NH2:13])=[CH:11][C:10]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:9][N:8]=2)[CH2:3][CH2:2]1.Cl[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[F:31])[N:24]=[C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[C:22]=1[CH3:38].Cl.O1CCOCC1.CN1C(=O)CCC1>>[N:4]1([C:7]2[C:12]([NH:13][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][C:29]=4[F:31])[N:24]=[C:23]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=4)[C:22]=3[CH3:38])=[CH:11][C:10]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[CH:9][N:8]=2)[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 312751,4-DioxaneHCID 596310462,5-Dimorpholinopyridin-3-amineHCID 596312094-Chloro-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

Product 1

HCID 59631586N-(2,5-di-4-morpholinyl-3-pyridinyl)-5-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine

Procedure

Prepared according to Procedure K, method 2 using 2,5-dimorpholinopyridin-3-amine (157 mg, 0.594 mmol; described herein), 4-chloro-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (162 mg, 0.59 mmol; described herein), 4.0M hydrochloric acid in 1,4-dioxane (150 μL, 0.59 mmol), and NMP (590 μL, 7.1 mmol), and heating in a microwave at 160° for 3 h. Purification afforded N-(2,5-di-4-morpholinyl-3-pyridinyl)-5-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.70 (1H, d, J=4.7 Hz), 7.98 (1H, d, J=8.2 Hz), 7.87-7.93 (2H, m), 7.83 (1H, d, J=11.7 Hz), 7.55-7.65 (2H, m), 7.38 (1H, m), 7.13-7.24 (1H, m), 6.46 (1H, d, J=2.7 Hz), 3.88-4.03 (4H, m), 3.77-3.88 (4H, m), 3.01-3.28 (4H, br. s.), 3.04-3.14 (4H, m), 2.23 (3H, s). Mass Spectrum (ESI) m/e=501.2 (M+1).

Workup

  1. customPrepared
  2. temperatureheating in a microwave at 160° for 3 h
  3. customPurification

Sources & evidence

ORD record
ord-fb97bf6fcbd24754a9f054ee71354015
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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