Hydrazine hydrate (1:1) → HCID 44463106, compound

HRID 241384Notes

Reaction equation

HRID 241384 reaction equation
[CH:1]([C:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=2[S:6][C:5]=1[CH2:17][CH2:18][C:19]1[C:23]2[CH:24]=[C:25]([CH3:33])[C:26]([CH:28]=[CH:29][C:30]([OH:32])=[O:31])=[CH:27][C:22]=2[O:21][N:20]=1)([CH3:3])[CH3:2].O.NN>CO.Cl>[CH:1]([C:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:14])([F:15])[F:16])=[CH:12][C:7]=2[S:6][C:5]=1[CH2:17][CH2:18][C:19]1[C:23]2[CH:24]=[C:25]([CH3:33])[C:26]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:27][C:22]=2[O:21][N:20]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66884349HCID 66884349, compound

Product 1

HCID 44463106HCID 44463106, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of the above-mentioned 3-[3-[2-[3-isopropyl-6-(trifluoromethyl)benzothiophen-2-yl]ethyl]-5-methylbenzisoxazol-6-yl]acrylic acid (75 mg, 0.15 mmol) in MeOH (0.8 mL) was added hydrazine monohydrate (0.15 mL, 3.1 mmol). The mixture was heated reflux for 4 hours, cooled to room temperature, diluted with ice-water and 1M HCl, and extracted with ethyl acetate. The organic layer was collected, washed with brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the titled compound as a brown oil (57 mg, yield 78%).

Workup

  1. temperatureThe mixture was heated
  2. temperaturereflux for 4 hours
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was collected
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0ff5cf5a44f740bf902dd249a5a69d04
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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