Methanol → (S)-((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-aminopropanoate maleate

HRID 1517813Notes

Reaction equation

HRID 1517813 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:21][C:22]([C:24]2[C:25](=[O:45])[N:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:27]([CH2:30][C@H:31]([O:33][C:34](=[O:38])[C@@H:35]([NH2:37])[CH3:36])[CH3:32])[C:28]=2[CH3:29])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.CO.[C:48]([OH:55])(=[O:54])/[CH:49]=[CH:50]\[C:51]([OH:53])=[O:52]>CCOC(C)=O>[C:48]([OH:55])(=[O:54])/[CH:49]=[CH:50]\[C:51]([OH:53])=[O:52].[F:1][C:2]1[CH:3]=[C:4]([NH:21][C:22]([C:24]2[C:25](=[O:45])[N:26]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[N:27]([CH2:30][C@H:31]([O:33][C:34](=[O:38])[C@@H:35]([NH2:37])[CH3:36])[CH3:32])[C:28]=2[CH3:29])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 444266Maleic AcidHCID 46937494(S)-((R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenyl carbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-aminopropanoate

Product 1

HCID 46937599(S)-((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-aminopropanoate maleateYield 85.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)—((R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenyl carbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-amino-propanoate (61.3 mg, 0.1 mmol) in EtOAc (15 mL)/MeOH (10 mL) was added maleic acid (23.2 mg, 0.2 mmol, Shantou Xilong chemical factory). After stirring for 40 min, the mixture was concentrated in vacuo, and the resulted oil was washed with a mixture of MeOH (2 mL)/EtOAc (10 mL) followed by EtOAc (5 mL×3) to give the title compound as yellow oil (62.6 mg, 85.6%).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. washthe resulted oil was washed with a mixture of MeOH (2 mL)/EtOAc (10 mL)

Sources & evidence

ORD record
ord-9d8931f2b76f4fdf9731de9a21c803b7
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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