Hydrochloric Acid → HCID 59631175, compound

HRID 1431280Notes

Reaction equation

HRID 1431280 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[C:3]=1[CH3:21].[O:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:30][C:29]=2[NH2:40])[CH2:24][CH2:23]1.Cl.O1CCOCC1>CO>[N:25]1([C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)=[CH:30][C:29]=2[NH:40][C:2]2[C:11]3[C:6](=[CH:7][C:8]([F:13])=[C:9]([F:12])[CH:10]=3)[N:5]=[C:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:3]=2[CH3:21])[CH2:26][CH2:27][O:22][CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 288098152,5-DimorpholinobenzenamineHCID 59631348HCID 59631348, compound

Product 1

HCID 59631175HCID 59631175, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to Procedure K, Method 1 using 4-chloro-6,7-difluoro-2-(2-fluorophenyl)-3-methylquinoline (100 mg, 325 μmol), 2,5-dimorpholinobenzenamine (86 mg, 325 μmol) and 4N hydrochloric acid solution in dioxane (0.081 mL, 325 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 7.91 (1H, dd, J=11.0, 7.8 Hz), 7.55-7.71 (2H, m), 7.43-7.54 (1H, m, J=7.9, 7.9, 5.4, 2.0 Hz), 7.31-7.40 (1H, m), 7.09-7.25 (3H, m), 6.46 (1H, dd, J=8.6, 2.7 Hz), 6.01 (1H, br. s.), 3.87-4.05 (4H, m), 3.73-3.83 (4H, m), 3.06 (4H, dd, J=2.5, 1.8 Hz), 2.90-3.01 (4H, m), 2.21 (3H, d, J=2.0 Hz). Mass Spectrum (ESI) m/e=535.3 (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-4108f28ef74a4fb78742bf248133bebf
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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