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

HRID 1354314
Notes
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Reaction equation

HRID 1354314 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+].Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 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 887
Methanol
Solvent
2×

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) added 1M sodium hydroxide solution (4 ml) and heated to 70° C. for 30 min. Removed methanol under vacuum and acidified solution to pH 4 with 6M hydrochloric acid. Filtered solid, washed with water and oven dried to give 137 mg product.

Workup

  1. filtrationFiltered solid
  2. washwashed with water and oven
  3. customdried

Sources & evidence

ORD record
ord-95f3b5a5282a4786997e801adc88ae8a
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07223766B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes