Hydrochloric Acid → HCID 59631530, compound

HRID 1431276Notes

Reaction equation

HRID 1431276 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][CH: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>CO>[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][CH: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 12378945HCID 12378945, compoundHCID 288098152,5-Dimorpholinobenzenamine

Product 1

HCID 59631530HCID 59631530, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to Procedure K, Method 1 using 4-chloro-3-methyl-2-phenylquinoline (150 mg, 591 μmol), 2,5-dimorpholinobenzenamine (156 mg, 591 μmol) and 4N hydrochloric acid solution in dioxane (0.15 mL, 591 μmol) in MeOH (3.00 mL) to afford product as a colorless solid after purification by chromatography on silica gel eluting with MeOH gradient in DCM. 1H NMR (400 MHz, chloroform-d) δ ppm 8.18 (1H, d, J=8.2 Hz), 7.90 (1H, dd, J=8.6, 1.2 Hz), 7.69 (1H, td, J=7.6, 1.2 Hz), 7.59-7.66 (2H, m), 7.41-7.57 (4H, m), 7.23 (1H, s), 7.12 (1H, d, J=8.6 Hz), 6.44 (1H, dd, J=8.6, 2.7 Hz), 6.04 (1H, d, J=2.7 Hz), 3.88-4.01 (4H, m), 3.69-3.80 (4H, m), 3.02-3.16 (4H, m), 2.88-3.00 (4H, m), 2.32 (3H, s). Mass Spectrum (ESI) m/e=481.3 (M+1).

Workup

  1. customPrepared
  2. customto afford product as a colorless solid
  3. customafter purification by chromatography on silica gel eluting with MeOH gradient in DCM

Sources & evidence

ORD record
ord-e3e9e652c5d144cabe5636fda11f5934
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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