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

HRID 1517866Notes

Reaction equation

HRID 1517866 reaction equation
C(OC([NH:8][CH2:9][C:10]([O:12][C:13]1([CH2:16][CH2:17][O:18][C:19]2[CH:28]=[C:27]3[C:22]([C:23]([O:29][C:30]4[CH:35]=[CH:34][C:33]([NH:36][C:37]([C:39]5[C:40](=[O:52])[N:41]([C:46]6[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=6)[N:42]([CH3:45])[C:43]=5[CH3:44])=[O:38])=[CH:32][C:31]=4[F:53])=[CH:24][CH:25]=[N:26]3)=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)=[O:11])=O)(C)(C)C.[ClH:54]>C(OCC)(=O)C>[ClH:54].[NH2:8][CH2:9][C:10]([O:12][C:13]1([CH2:16][CH2:17][O:18][C:19]2[CH:28]=[C:27]3[C:22]([C:23]([O:29][C:30]4[CH:35]=[CH:34][C:33]([NH:36][C:37]([C:39]5[C:40](=[O:52])[N:41]([C:46]6[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=6)[N:42]([CH3:45])[C:43]=5[CH3:44])=[O:38])=[CH:32][C:31]=4[F:53])=[CH:24][CH:25]=[N:26]3)=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666938911-(2-(4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)quinolin-7-yloxy)ethyl)cyclopropyl 2-(tert-butoxy-carbonylamino)acetate

Product 1

HCID 666933811-(2-(4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)quinolin-7-yloxy)ethyl)cyclopropyl 2-aminoacetate hydrochlorideYield 30.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1-(2-(4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)quinolin-7-yloxy)ethyl)cyclopropyl 2-(tert-butoxy-carbonylamino)acetate (190 mg, 0.262 mmol) in 8 mL of ethyl acetate was added a solution of HCl in 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 (20 mL×3) to afford the title compound as a white solid (54 mg, 30.3%).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with ethyl acetate (20 mL×3)

Sources & evidence

ORD record
ord-b1b45e45b0be47f7b23f2cbae525ea7e
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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