Hydrochloric Acid → 7-Fluoro-3-methyl-N-(2-(4-morpholinyl)-5-(4-thiomorpholinyl)-3-pyridinyl)-2-(2-pyridinyl)-4-quinolinamine

HRID 1431260Notes

Reaction equation

HRID 1431260 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:18]=[CH:17][CH:16]=[CH:15][N:14]=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][S:36][CH2:35][CH2:34]3)=[CH:28][N:27]=2)[CH2:22][CH2:21]1.Cl.O1CCOCC1>CN1C(=O)CCC1>[F:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:32][C:31]3[C:26]([N:23]4[CH2:22][CH2:21][O:20][CH2:25][CH2:24]4)=[N:27][CH:28]=[C:29]([N:33]4[CH2:34][CH2:35][S:36][CH2:37][CH2:38]4)[CH:30]=3)=[C:3]([CH3:19])[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:5]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 596310754-Chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinolineHCID 596313712-(4-morpholinyl)-5-(4-thiomorpholinyl)-3-Pyridinamine

Product 1

HCID 509057167-Fluoro-3-methyl-N-(2-(4-morpholinyl)-5-(4-thiomorpholinyl)-3-pyridinyl)-2-(2-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-2-yl)quinoline (117 mg, 0.43 mmol), 2-morpholino-5-thiomorpholinopyridin-3-amine (120 mg, 0.43 mmol) and a 4.0M solution of HCl in dioxane (0.11 mL, 0.43 mmol) in NMP (1.0 mL) and heating in the microwave for 2 h at 150° C. After purification 7-fluoro-3-methyl-N-(2-(4-morpholinyl)-5-(4-thiomorpholinyl)-3-pyridinyl)-2-(2-pyridinyl)-4-quinolinamine was obtained. 1H NMR (400 MHz, chloroform-d) δ ppm 8.74 (1H, dd, J=4.1, 1.0 Hz), 7.85-7.96 (2H, m), 7.75-7.84 (2H, m), 7.58 (1H, d, J=2.7 Hz), 7.40 (1H, ddd, J=7.0, 4.9, 1.8 Hz), 7.28-7.32 (1H, m), 6.74 (1H, s), 6.19 (1H, d, J=2.7 Hz), 3.93 (4H, t, J=4.7 Hz), 3.31 (4H, ddd, J=4.9, 2.7, 2.5 Hz), 3.23 (4H, br. s.), 2.63 (4H, dt, J=5.1, 2.5 Hz), 2.38 (3H, s). Mass Spectrum (ESI) m/e=517.0 (M+1).

Workup

  1. customPrepared
  2. customAfter purification 7-fluoro-3-methyl-N-(2-(4-morpholinyl)-5-(4-thiomorpholinyl)-3-pyridinyl)-2-(2-pyridinyl)-4-quinolinamine
  3. customwas obtained

Sources & evidence

ORD record
ord-f658ace77a0a4d82aaf95c0d2fab7207
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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