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Sodium Hydroxide → 4-[6-(5-Chloro-2-fluoro-phenyl)-3-methyl-isoxazolo[5,4-d]pyrimidin-4-ylamino]-nicotinic acid

HRID 1010847
Notes
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Reaction equation

HRID 1010847 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=3[F:24])[N:14]=[C:13]3[O:25][N:26]=[C:27]([CH3:28])[C:12]=23)=[CH:8][CH:7]=[N:6][CH:5]=1.[OH-].[Na+]>CO>[Cl:23][C:21]1[CH:20]=[CH:19][C:18]([F:24])=[C:17]([C:15]2[N:14]=[C:13]3[O:25][N:26]=[C:27]([CH3:28])[C:12]3=[C:11]([NH:10][C:9]3[C:4]([C:3]([OH:29])=[O:2])=[CH:5][N:6]=[CH:7][CH:8]=3)[N:16]=2)[CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 588659594-[6-(5-Chloro-2-fluoro-phenyl)-3-methyl-isoxazolo[5,4-d]pyrimidin-4-ylamino]-nicotinic acid methyl ester

Product 1

HCID 211043334-[6-(5-Chloro-2-fluoro-phenyl)-3-methyl-isoxazolo[5,4-d]pyrimidin-4-ylamino]-nicotinic acidYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

4-[6-(5-Chloro-2-fluoro-phenyl)-3-methyl-isoxazolo[5,4-d]pyrimidin-4-ylamino]-nicotinic acid methyl ester (525 mg) was suspended in methanol (4 ml), 1M sodium hydroxide solution (4 ml) was added, and then heated to 70° C. for 30 min. The methanol was removed under vacuum and the solution was acidified to pH 4 with 6 M hydrochloric acid. The solid was filtered, washed with water and dried in the oven to give 137 mg product.

Workup

  1. customThe methanol was removed under vacuum
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried in the oven

Sources & evidence

ORD record
ord-9cce29f57b184312b2209e3907df1ae4
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977342B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes