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

HRID 1517878Notes

Reaction equation

HRID 1517878 reaction equation
C(OC([NH:8][CH2:9][C:10]([O:12][C:13]1([CH2:16][O:17][C:18]2[CH:27]=[C:26]3[C:21]([C:22]([O:28][C:29]4[CH:34]=[CH:33][C:32]([NH:35][C:36]([C:38]5[C:39](=[O:51])[N:40]([C:45]6[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=6)[N:41]([CH3:44])[C:42]=5[CH3:43])=[O:37])=[CH:31][C:30]=4[F:52])=[CH:23][CH:24]=[N:25]3)=[CH:20][CH:19]=2)[CH2:15][CH2:14]1)=[O:11])=O)(C)(C)C.[ClH:53]>C(OCC)(=O)C>[ClH:53].[NH2:8][CH2:9][C:10]([O:12][C:13]1([CH2:16][O:17][C:18]2[CH:27]=[C:26]3[C:21]([C:22]([O:28][C:29]4[CH:34]=[CH:33][C:32]([NH:35][C:36]([C:38]5[C:39](=[O:51])[N:40]([C:45]6[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=6)[N:41]([CH3:44])[C:42]=5[CH3:43])=[O:37])=[CH:31][C:30]=4[F:52])=[CH:23][CH:24]=[N:25]3)=[CH:20][CH:19]=2)[CH2:14][CH2:15]1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666938521-((4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)quinolin-7-yloxy)methyl)cyclopropyl 2-(tert-butoxycarbonylamino)acetate

Product 1

HCID 666937951-((4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)quinolin-7-yloxy)methyl)cyclopropyl 2-aminoacetate hydrochlorideYield 15%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The compound 1-((4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)quinolin-7-yloxy)methyl)cyclopropyl 2-(tert-butoxycarbonylamino)acetate (80 mg, 0.112 mmol) was dissolved in ethyl acetate (8 mL). 2 mL of HCl in ethyl acetate (0.93 mol/L) was added dropwise and the reaction was stirred at rt for 30 minute. The solid was collected by filtration and washed with ethyl acetate (10 mL×2) to afford the title compound as a white solid (11 mg, 15%).

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with ethyl acetate (10 mL×2)

Sources & evidence

ORD record
ord-3909fe6518884925aa554011ac272e26
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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