Hydrochloric Acid → 2-(2-Fluorophenyl)-3-methyl-N-(2-(4-morpholinyl)-5-(3-pyridinyl)phenyl)-4-quinolinamine

HRID 1431251Notes

Reaction equation

HRID 1431251 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[C:3]=1[CH3:19].[O:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:32]=[CH:31][C:30]([C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)=[CH:29][C:27]=2[NH2:28])[CH2:22][CH2:21]1.Cl.O1CCOCC1>CN1C(=O)CCC1>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:4]1[C:3]([CH3:19])=[C:2]([NH:28][C:27]2[CH:29]=[C:30]([C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)[CH:31]=[CH:32][C:26]=2[N:23]2[CH2:24][CH2:25][O:20][CH2:21][CH2:22]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 596310952-Morpholino-5-(pyridin-3-yl)anilineHCID 596311684-Chloro-2-(2-fluorophenyl)-3-methylquinoline

Product 1

HCID 596313772-(2-Fluorophenyl)-3-methyl-N-(2-(4-morpholinyl)-5-(3-pyridinyl)phenyl)-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Prepared according to general Procedure K using 4-chloro-2-(2-fluorophenyl)-3-methylquinoline (64 mg, 0.23 mmol), 2-morpholino-5-(pyridin-3-yl)aniline (60 mg, 0.23 mmol) and a 4.0M solution of HCl in dioxane (0.06 mL, 0.23 mmol) in NMP (1.0 mL) and heating in the microwave for 2 h at 150° C. After purification 2-(2-fluorophenyl)-3-methyl-N-(2-(4-morpholinyl)-5-(3-pyridinyl)phenyl)-4-quinolinamine was obtained. 1H NMR (400 MHz, chloroform-d) δ ppm 8.49 (1H, dd, J=4.7, 1.6 Hz), 8.19 (1H, d, J=8.2 Hz), 7.92 (1H, d, J=8.2 Hz), 7.59-7.76 (4H, m), 7.54 (1H, d, J=7.4 Hz), 7.47 (1H, d, J=8.2 Hz), 7.31-7.36 (1H, m), 7.10-7.24 (4H, m), 6.65 (1H, br. s.), 3.97 (4H, t, J=4.7 Hz), 3.09-3.30 (4H, m), 2.26 (3H, d, J=2.3 Hz). Mass Spectrum (ESI) m/e=491.0 (M+1).

Workup

  1. customPrepared
  2. customAfter purification 2-(2-fluorophenyl)-3-methyl-N-(2-(4-morpholinyl)-5-(3-pyridinyl)phenyl)-4-quinolinamine
  3. customwas obtained

Sources & evidence

ORD record
ord-59610dc2934b48189d9aac67a5964d9b
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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