Hydrochloric Acid → (R)-1-(4-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl 2-aminoacetate hydro-chloride

HRID 1517885Notes

Reaction equation

HRID 1517885 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[C:26](=[O:52])[N:27]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[N:28]([CH2:31][C@H:32]([O:34][C:35](=[O:45])[CH2:36][NH:37]C(OC(C)(C)C)=O)[CH3:33])[C:29]=2[CH3:30])=[O:24])=[CH:18][C:17]=1[F:53].[ClH:54]>CCOC(C)=O>[ClH:54].[NH2:37][CH2:36][C:35]([O:34][C@H:32]([CH3:33])[CH2:31][N:28]1[C:29]([CH3:30])=[C:25]([C:23](=[O:24])[NH:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[C:17]([F:53])[CH:18]=2)[C:26](=[O:52])[N:27]1[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)=[O:45]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68739076HCID 68739076, compound

Product 1

HCID 66670514(R)-1-(4-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl 2-aminoacetate hydro-chlorideYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (R)-1-(4-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl-2-(tert-butoxycarbonyl amino)acetate (100 mg, 0.137 mmol) in EtOAc (15 mL) was added 3 mL of saturated HCl in EtOAc (3 mL). The reaction mixture was stirred at rt overnight. The solid formed was collected and was crystallized in MeOH/EtOAc (20 mL, v/v=1:5). The product was further washed with EtOAc (5 mL×3) and dried under vacuum overnight to afford the title compound as a white solid (88 mg, 83%).

Workup

  1. customThe solid formed
  2. customwas collected
  3. customwas crystallized in MeOH/EtOAc (20 mL, v/v=1:5)
  4. washThe product was further washed with EtOAc (5 mL×3)
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-c256a498b5f645548016d6e88e8fa752
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

Loading…