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

HRID 1431381Notes

Reaction equation

HRID 1431381 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][C:27]([F:31])=[CH:28][CH:29]=2)[N:24]=[C:23]([C:32]2[CH:33]=[N:34][CH:35]=[C:36]([F:38])[CH:37]=2)[C:22]=1[CH3:39].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][C:27]([F:31])=[CH:28][CH:29]=4)[N:24]=[C:23]([C:32]4[CH:33]=[N:34][CH:35]=[C:36]([F:38])[CH:37]=4)[C:22]=3[CH3:39])=[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 596314314-Chloro-7-fluoro-2-(5-fluoropyridin-3-yl)-3-methylquinoline

Product 1

HCID 59631273N-(2,5-di-4-morpholinyl-3-pyridinyl)-7-fluoro-2-(5-fluoro-3-pyridinyl)-3-methyl-4-quinolinamine

Conditions

Temperature
150 °C

Procedure

Prepared according to Procedure K, method 2 using 2,5-dimorpholinopyridin-3-amine (43 mg, 0.16 mmol; described herein), 4-chloro-7-fluoro-2-(5-fluoropyridin-3-yl)-3-methylquinoline (47 mg, 0.16 mmol; described herein), 4.0M hydrochloric acid in 1,4-dioxane (4 μL, 0.1 equiv, 16 μmol), and NMP (190 μL, 1.9 mmol). The reaction was heated in a microwave at 150° C. for 4 h. Purification afforded N-(2,5-di-4-morpholinyl-3-pyridinyl)-7-fluoro-2-(5-fluoro-3-pyridinyl)-3-methyl-4-quinolinamine as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.69 (1H, m), 8.60 (1H, d, J=2.7 Hz), 7.84 (1H, m), 7.76 (2H, m), 7.64 (1H, d, J=2.7 Hz), 7.33 (1H, m), 6.81 (1H, s), 6.21 (1H, d, J=2.7 Hz), 3.89-3.97 (4H, m), 3.72-3.79 (4H, m), 3.24 (4H, m), 2.89-2.98 (4H, m), 2.33 (3H, s). Mass Spectrum (ESI) m/e=519.0 (M+1).

Workup

  1. customPrepared
  2. customPurification

Sources & evidence

ORD record
ord-114354c6bb434f13aafb34f9d56947d4
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…