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 4-methylbenzenesulfonate

HRID 1517807Notes

Reaction equation

HRID 1517807 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]1([CH3:58])[CH:53]=[CH:52][C:51]([S:54]([OH:57])(=[O:56])=[O:55])=[CH:50][CH:49]=1>CCOC(C)=O>[CH3:58][C:48]1[CH:49]=[CH:50][C:51]([S:54]([OH:57])(=[O:56])=[O:55])=[CH:52][CH:53]=1.[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 6101p-Toluenesulfonic 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 86645593(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 4-methylbenzenesulfonateYield 75.8%

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-aminopropanoate (61.3 mg, 0.1 mmol) in EtOAc (15 mL)/MeOH (10 mL) was added p-toluene sulfonic acid (38 mg, 0.2 mmol, Shanghai chemical reagent 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 (59.6 mg, 60%).

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-a2b2dd42220e48c098c7eb20745ef314
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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