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Sodium Hydroxide → HCID 60053887, compound

HRID 34136
Notes
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Reaction equation

HRID 34136 reaction equation
C[O:2][C:3]([C:5]1([NH:8][C:9]([C:11]2[C:12]([O:29][CH3:30])=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[C:14]3/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:10])[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>O1CCCC1.CO.O>[F:28][C:25]1[CH:24]=[CH:23][C:22](/[CH:21]=[CH:20]/[C:14]2[C:13]3[C:17](=[CH:18][CH:19]=[C:11]([C:9]([NH:8][C:5]4([C:3]([OH:4])=[O:2])[CH2:7][CH2:6]4)=[O:10])[C:12]=3[O:29][CH3:30])[NH:16][N:15]=2)=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 60053859methyl 1-[[3-[(E)-2-(4-fluorophenyl)ethenyl]-4-methoxy-1H-indazole-5-carbonyl]amino]cyclopropane-1-carboxylate

Product 1

HCID 60053887HCID 60053887, compoundYield 78.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a mixed solution of 200 mg of 1-({3-[(E)-2-(4-fluorophenyl)-vinyl]-4-methoxy-1H-indazol-5-carbonyl}-amino)-cyclopropane carboxylic acid methyl ester obtained in Example 1317 in 5 ml of tetrahydrofuran and 2 ml of methanol was added 2 ml of a 1N sodium hydroxide aqueous solution, followed by stirring at room temperature overnight. The reaction mixture was diluted with water and the aqueous layer was washed with diethyl ether. The aqueous layer was adjusted to pH 2 by adding 1N hydrochloric acid, and the precipitated solid was collected by filtration with glass filter. The solid was washed with water and was dried under reduced pressure, to give 151 mg of the title compound as a brown solid.

Workup

  1. washthe aqueous layer was washed with diethyl ether
  2. additionby adding 1N hydrochloric acid
  3. filtrationthe precipitated solid was collected by filtration with glass
  4. filtrationfilter
  5. washThe solid was washed with water
  6. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-bf3fc7c1c15c4d7580136665173122ab
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429609B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes