Hydrochloric Acid → HCID 11691110, compound

HRID 1788234Notes

Reaction equation

HRID 1788234 reaction equation
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[C:11]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=2[Cl:29])=[C:12]([F:20])[C:13]2[O:17][N:16]=[C:15]([CH3:18])[C:14]=2[CH:19]=1)=[O:9])=C.Cl.[OH-].[Na+]>CCO.CCOC(C)=O>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[C:11]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=2[Cl:29])=[C:12]([F:20])[C:13]2[O:17][N:16]=[C:15]([CH3:18])[C:14]=2[CH:19]=1)=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86596775HCID 86596775, compound

Product 1

HCID 11691110HCID 11691110, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methylbenzo[d]isoxazole-5-carboxylic acid (2-vinyloxyethoxy)amide (11a) (55.4 mg, 0.114 mmol) and aqueous HCl (1 M, 0.23 mL) in EtOH (3 mL) was stirred for 2 hours at room temperature. The pH of the reaction mixture was adjusted to 6-7 with aqueous NaOH (2 N). The reaction was diluted with EtOAc. The organic layer was washed with water, dried over MgSO4, filtered, and concentrated in vacuo to give 50.2 mg (96% yield) of the desired product (12a). MS APCI (−) m/z 456, 458 (M+, Br, Cl pattern) detected: 1H NMR (400 MHz, CD3OD) δ 7.87 (s, 1H), 7.57 (d, 1H), 7.31 (dd, 1H), 6.74 (dd, 1H), 4.01 (t, 2H), 3.74 (t, 2H), 2.60 (s, 3H): 19F NMR (376 MHz, CD3OD) −140.85 (s, 1F).

Workup

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

Sources & evidence

ORD record
ord-6a11d70221454b7eba07112121f29d8a
Source dataset
uspto-grants-2009_03
Patent number
US07511058B2

Reaction notes

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