Maleic Acid → HCID 66669977, compound

HRID 1517855Notes

Reaction equation

HRID 1517855 reaction equation
[CH3:1][NH:2][CH2:3][C:4]([O:6][C@H:7]([CH3:44])[CH2:8][N:9]1[C:13]([CH3:14])=[C:12]([C:15](=[O:36])[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)=[CH:19][N:18]=2)[C:11](=[O:37])[N:10]1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:5].[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49]>CO>[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49].[CH3:1][NH:2][CH2:3][C:4]([O:6][C@H:7]([CH3:44])[CH2:8][N:9]1[C:13]([CH3:14])=[C:12]([C:15](=[O:36])[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)=[CH:19][N:18]=2)[C:11](=[O:37])[N:10]1[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:5]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 46938058HCID 46938058, compound

Product 1

HCID 66669977HCID 66669977, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-1-(4-(5-(7-methoxyquinolin-4-yloxy)pyridin-2-ylcarbamoyl)-2,3-dihydro-5-methyl-3-oxo-2-phenylpyrazol-1-yl)propan-2-yl 2-(methylamino)acetate (80 mg, 0.134 mmol) in MeOH (10 mL) was added maleic acid (46.74 mg, 0.40 mmol, Shanghai San'aisi Reagent Co., Ltd). After stirring for 40 min, the reaction mixture was concentrated in vacuo. The resulted residue was recrystallized in a mixture of MeOH (4 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 (68.8 mg, 67%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe resulted residue was recrystallized in a mixture of MeOH (4 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-d3a100af36c14845b34c8410f67cb8f4
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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