Hydrochloric Acid → 3-((5-Fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)-2-pyridinecarbonitrile

HRID 1431257Notes

Reaction equation

HRID 1431257 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:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:3]=1[CH3:19].[NH2:20][C:21]1[C:22]([C:33]#[N:34])=[N:23][CH:24]=[C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:26]=1.Cl.O1CCOCC1>CN1C(=O)CCC1>[F:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([NH:20][C:21]1[C:22]([C:33]#[N:34])=[N:23][CH:24]=[C:25]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[CH:26]=1)=[C:3]([CH3:19])[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[N:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 596312094-Chloro-5-fluoro-3-methyl-2-(pyridin-2-yl)quinolineHCID 596312623-Amino-5-morpholinopicolinonitrile

Product 1

HCID 509054993-((5-Fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)-2-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Prepared according to general Procedure K using 4-chloro-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (93 mg, 0.34 mmol), 3-amino-5-morpholinopicolinonitrile (70 mg, 0.34 mmol) and a 4.0M solution of HCl in dioxane (0.08 mL, 0.34 mmol) in NMP (1.0 mL) and heating in the microwave for 2 h at 150° C. After purification 3-((5-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)-2-pyridinecarbonitrile was obtained. 1H NMR (400 MHz, chloroform-d) δ ppm 8.68 (1H, dt, J=3.1, 1.6 Hz), 8.00 (1H, d, J=8.6 Hz), 7.87-7.97 (3H, m), 7.64 (1H, td, J=8.2, 5.5 Hz), 7.39 (1H, ddd, J=7.0, 4.9, 1.8 Hz), 7.17-7.32 (2H, m), 6.23 (1H, d, J=2.3 Hz), 3.75-3.86 (4H, m), 3.17-3.31 (4H, m), 2.29 (3H, s). Mass Spectrum (ESI) m/e=441.1 (M+1).

Workup

  1. customPrepared
  2. customAfter purification 3-((5-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)-2-pyridinecarbonitrile
  3. customwas obtained

Sources & evidence

ORD record
ord-6453230b43534e2cb1740b7d39d58120
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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