Hydrochloric Acid → HCID 59631215, compound

HRID 1431287Notes

Reaction equation

HRID 1431287 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][N:13]=2)[C:3]=1[CH3:18].[O:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[CH:27][C:26]=2[NH2:37])[CH2:21][CH2:20]1.Cl.O1CCOCC1>CN1C(=O)CCC1>[N:22]1([C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[CH:27][C:26]=2[NH:37][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[C:3]=2[CH3:18])[CH2:23][CH2:24][O:19][CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 288098152,5-DimorpholinobenzenamineHCID 59631328HCID 59631328, compound

Product 1

HCID 59631215HCID 59631215, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Prepared according to Procedure K, Method 2 using 4-chloro-3-methyl-2-(pyridin-2-yl)quinoline (77 mg, 302 μmol), 2,5-dimorpholinobenzenamine (80 mg, 302 μmol) and 4N hydrochloric acid solution in dioxane (7.6 μL, 30 μmol) in NMP (1 mL) to afford product as a colorless solid upon purification by reversed phase HPLC. 1H NMR (400 MHz, chloroform-d) δ ppm 8.58-8.72 (1H, m), 8.13 (1H, d, J=8.6 Hz), 7.74-7.90 (3H, m), 7.54-7.68 (1H, m), 7.39 (1H, td, J=7.6, 1.2 Hz), 7.25-7.35 (1H, m), 7.15 (1H, s), 7.02 (1H, d, J=8.6 Hz), 6.35 (1H, dd, J=8.6, 2.7 Hz), 5.95 (1H, d, J=2.7 Hz), 3.74-3.93 (4H, m), 3.52-3.72 (4H, m), 2.99 (4H, d, J=3.9 Hz), 2.72-2.89 (4H, m), 2.31 (3H, s). Mass Spectrum (ESI) m/e=482.2 (M+1).

Workup

  1. customPrepared
  2. customto afford product as a colorless solid
  3. customupon purification by reversed phase HPLC

Sources & evidence

ORD record
ord-0c2006a2c3db48588bb51974a697dade
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…