Hydrochloric Acid → (R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl 2-(dimethylamino)acetate hydrochloride

HRID 1517848Notes

Reaction equation

HRID 1517848 reaction equation
[CH3:1][N:2]([CH3:46])[CH2:3][C:4]([O:6][C@H:7]([CH3:45])[CH2:8][N:9]1[C:13]([CH3:14])=[C:12]([C:15](=[O:37])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[C:33]4[C:28](=[CH:29][C:30]([O:34][CH3:35])=[CH:31][CH:32]=4)[N:27]=[CH:26][CH:25]=3)=[C:19]([F:36])[CH:18]=2)[C:11](=[O:38])[N:10]1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:5].[ClH:47]>CO.CCOC(C)=O>[ClH:47].[CH3:46][N:2]([CH3:1])[CH2:3][C:4]([O:6][C@H:7]([CH3:45])[CH2:8][N:9]1[C:13]([CH3:14])=[C:12]([C:15](=[O:37])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[C:33]4[C:28](=[CH:29][C:30]([O:34][CH3:35])=[CH:31][CH:32]=4)[N:27]=[CH:26][CH:25]=3)=[C:19]([F:36])[CH:18]=2)[C:11](=[O:38])[N:10]1[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 46938003(R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl 2-(dimethylamino)acetate

Product 1

HCID 66669912(R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl 2-(dimethylamino)acetate hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (R)-1-(4-(4-(7-methoxyquinolin-4-yloxy)-3-fluorophenylcarbamoyl)-2,3-dihydro-5-methyl-3-oxo-2-phenylpyrazol-1-yl)propan-2-yl 2-(dimethylamino)acetate (100 mg, 0.16 mmol) in a mixture of MeOH (10 mL)/EtOAc (15 mL) was added a saturated solution of HCl in EtOAc (5 mL). After stirring for 40 minutes, the resulted mixture was concentrated in vacuo. The residue was recrystallized in a mixture of MeOH (2 mL)/EtOAc (8 mL). The solid was collected by filtration, washed with EtOAc (5 mL×3) and dried under vacuum overnight. The title compound was obtained as a yellow solid (90.1 mg, 80%).

Workup

  1. concentrationthe resulted mixture was concentrated in vacuo
  2. customThe residue was recrystallized in a mixture of MeOH (2 mL)/EtOAc (8 mL)
  3. filtrationThe solid was collected by filtration
  4. washwashed with EtOAc (5 mL×3)
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-11911fc53c414de18eabf6f2737a2617
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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