Hydrochloric Acid → HCID 59631590, compound

HRID 1431283Notes

Reaction equation

HRID 1431283 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:3]=1[CH3:20].[O:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:29][C:28]=2[NH2:39])[CH2:23][CH2:22]1.Cl.O1CCOCC1>CO>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:39][C:28]3[CH:29]=[C:30]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH:31]=[CH:32][C:27]=3[N:24]3[CH2:23][CH2:22][O:21][CH2:26][CH2:25]3)=[C:3]([CH3:20])[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])=[N:5]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 288098152,5-DimorpholinobenzenamineHCID 59631282HCID 59631282, compound

Product 1

HCID 59631590HCID 59631590, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to Procedure K, Method 1 using 4,7-dichloro-2-(2-fluorophenyl)-3-methylquinoline (125 mg, 408 μmol), 2,5-dimorpholinobenzenamine (108 mg, 408 μmol) and 4N hydrochloric acid solution in dioxane (0.10 mL, 408 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 8.02 (1H, d, J=2.3 Hz), 7.72 (1H, d, J=9.0 Hz), 7.46 (1H, td, J=7.4, 2.0 Hz), 7.26-7.40 (2H, m), 7.17-7.25 (1H, m), 7.13 (1H, s), 7.02-7.10 (1H, m), 6.98 (1H, d, J=8.6 Hz), 6.31 (1H, dd, J=8.6, 2.7 Hz), 5.91 (1H, br. s.), 3.77 (4H, t, J=4.7 Hz), 3.59-3.68 (4H, m), 2.91 (4H, br. s.), 2.74-2.87 (4H, m), 2.06 (3H, d, J=2.0 Hz). Mass Spectrum (ESI) m/e=533.2 (M+1).

Workup

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

Sources & evidence

ORD record
ord-05f4c96099ef4a5681d30c85de984a55
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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