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

HRID 1431249Notes

Reaction equation

HRID 1431249 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: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>CN1C(=O)CCC1>[N:23]1([C:26]2[C:31]([NH:32][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: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 596310524-Chloro-7-fluoro-3-methyl-2-(pyridin-3-yl)quinoline

Product 1

HCID 50905495N-(2,5-Di-4-morpholinyl-3-pyridinyl)-7-fluoro-3-methyl-2-(3-pyridinyl)-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Prepared according to general Procedure K using 4-chloro-7-fluoro-3-methyl-2-(pyridin-3-yl)quinoline (95 mg, 0.35 mmol), 2,5-dimorpholinopyridin-3-amine (92 mg, 0.35 mmol) and a 4.0M solution of HCl in dioxane (0.017 mL, 0.07 mmol) in NMP (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-3-methyl-2-(3-pyridinyl)-4-quinolinamine was obtained. 1H NMR (400 MHz, chloroform-d) δ ppm 8.87 (1H, d, J=2.7 Hz), 8.73 (1H, dd, J=5.1, 2.0 Hz), 7.99 (1H, dt, J=7.8, 2.0 Hz), 7.74-7.89 (2H, m), 7.62 (1H, d, J=2.7 Hz), 7.49 (1H, dd, J=8.0, 4.9 Hz), 7.31 (1H, ddd, J=9.3, 7.9, 2.7 Hz), 6.80 (1H, s), 6.21 (1H, d, J=2.7 Hz), 3.89-3.99 (4H, m), 3.75 (4H, ddd, J=4.3, 2.7, 2.3 Hz), 3.23 (4H, t, J=4.9 Hz), 2.87-3.01 (4H, m), 2.31 (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)-7-fluoro-3-methyl-2-(3-pyridinyl)-4-quinolinamine
  3. customwas obtained

Sources & evidence

ORD record
ord-ef90e03ca1f84f388162b725ee8cf191
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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