Hydrochloric Acid → HCID 50905935, compound

HRID 1431391Notes

Reaction equation

HRID 1431391 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][CH:27]=[CH:28][CH:29]=2)[N:24]=[C:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[C:22]=1[CH3:37].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][CH:27]=[CH:28][CH:29]=4)[N:24]=[C:23]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[C:22]=3[CH3:37])=[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 59631328HCID 59631328, compound

Product 1

HCID 50905935HCID 50905935, compound

Conditions

Temperature
165 °C

Procedure

Prepared according to Procedure K, method 2 using 2,5-dimorpholinopyridin-3-amine (63.5 mg, 0.24 mmol; described herein), 4-chloro-3-methyl-2-(pyridin-2-yl)quinoline (61.2 mg, 0.24 mmol; described herein), 4.0M hydrogen chloride in 1,4-dioxane (60 μL, 0.24 mmol), and NMP (280 μL, 2.9 mmol), and heating in a microwave at 165° C. for 3 h. Purification afforded N-(2,5-di-4-morpholinyl-3-pyridinyl)-3-methyl-2-(2-pyridinyl)-4-quinolinamine as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.74 (1H, d, J=4.7 Hz), 8.19 (1H, d, J=8.2 Hz), 7.85-7.95 (2H, m), 7.81 (1H, dd, J=8.2, 0.8 Hz), 7.71 (1H, td, J=7.6, 1.2 Hz), 7.59 (1H, d, J=2.7 Hz), 7.47-7.55 (1H, m), 7.34-7.45 (1H, m), 6.78 (1H, s), 6.24 (1H, d, J=2.7 Hz), 3.93 (4H, t, J=4.7 Hz), 3.73 (4H, ddd, J=4.3, 2.7, 2.3 Hz), 3.13-3.36 (4H, m), 2.87-3.01 (4H, m), 2.39 (3H, s). Mass Spectrum (ESI) m/e=483.2 (M+1).

Workup

  1. customPrepared
  2. customPurification

Sources & evidence

ORD record
ord-7eaf2d2b1fef4b58a884cb1b530f5c33
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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