Hydrochloric Acid → HCID 11567514, compound

HRID 1788232Notes

Reaction equation

HRID 1788232 reaction equation
C[O:2][C:3]([C:5]1[C:6]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=2[Cl:24])=[C:7]([F:15])[C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]=1)=[O:4].[Li+].[OH-].Cl>C1COCC1.O.O>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:6]2[C:5]([C:3]([OH:4])=[O:2])=[CH:14][C:9]3[C:10]([CH3:13])=[N:11][O:12][C:8]=3[C:7]=2[F:15])=[C:18]([Cl:24])[CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68861099HCID 68861099, compound

Product 1

HCID 11567514HCID 11567514, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methylbenzo[d]isoxazole-5-carboxylic acid methyl ester (8a) (200 mg, 0.48 mmol) in THF-water (3 mL/1.5 mL) was added aqueous LiOH (1 M, 1.00 mL) at room temperature. After 15 hours, the reaction mixture was acidified to pH 1 with aqueous HCl (1 M), diluted with water, and extracted with EtOAc/THF. The organic layer was washed with water, dried over MgSO4, filtered, and concentrated in vacuo to give 191.5 mg (99%) of the crude acid (9a) which was used without further purification. MS APCI (−) m/z 397, 399 (M+, Br, Cl pattern) detected: 1H NMR (400 MHz, DMSO-d6) δ 9.55 (s, 1H), 8.37 (s, 1H), 7.75 (s, 1H), 7.42 (d, 1H), 6.97 (t, 1H), 2.60 (s, 3H): 19F NMR (376 MHz, DMSO-d6) −140.15 (s, 1F).

Workup

  1. extractionextracted with EtOAc/THF
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2a16b9480d8433abd240eaab1ecc90f
Source dataset
uspto-grants-2009_03
Patent number
US07511058B2

Reaction notes

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