Hydrogen chloride-ethyl acetate → 1-(3-(4-(4-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)quinolin-7-yloxy)propyl)cyclopropyl 2-aminoacetate hydrochloride

HRID 1517870Notes

Reaction equation

HRID 1517870 reaction equation
C(OC([NH:8][CH2:9][C:10]([O:12][C:13]1([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24]([O:30][C:31]4[CH:36]=[CH:35][C:34]([NH:37][C:38]([C:40]5[C:44](=[O:45])[N:43]([C:46]6[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=6)[N:42]([CH3:52])[C:41]=5[CH3:53])=[O:39])=[CH:33][C:32]=4[F:54])=[CH:25][CH:26]=[N:27]3)=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)=[O:11])=O)(C)(C)C.[ClH:55].CCOC(C)=O>C(OCC)(=O)C>[ClH:55].[NH2:8][CH2:9][C:10]([O:12][C:13]1([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24]([O:30][C:31]4[CH:36]=[CH:35][C:34]([NH:37][C:38]([C:40]5[C:44](=[O:45])[N:43]([C:46]6[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=6)[N:42]([CH3:52])[C:41]=5[CH3:53])=[O:39])=[CH:33][C:32]=4[F:54])=[CH:25][CH:26]=[N:27]3)=[CH:22][CH:21]=2)[CH2:14][CH2:15]1)=[O:11]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 687430721-(3-(4-(4-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)quinolin-7-yloxy)propyl)cyclopropyl 2-(tert-but-oxycarbonylamino)acetate

Product 1

HCID 666933521-(3-(4-(4-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)quinolin-7-yloxy)propyl)cyclopropyl 2-aminoacetate hydrochlorideYield 37.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the mixture of 1-(3-(4-(4-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)quinolin-7-yloxy)propyl)cyclopropyl 2-(tert-but-oxycarbonylamino)acetate (160 mg, 0.216 mmol) in 8 mL of ethyl acetate was added a solution of HCl/EtOAc (0.93 mol/L, 5 mL) dropwise. The reaction mixture was stirred at rt for 30 minutes and then filtered. The solid was washed with ethyl acetate (10 mL×2) to afford the title compound as a white solid (55 mg, 37.9%).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with ethyl acetate (10 mL×2)

Sources & evidence

ORD record
ord-41d169993f904373bbb127742594fbcc
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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