Hydrochloric Acid → HCID 86684887, compound

HRID 238388Notes

Reaction equation

HRID 238388 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.O1CCCC1.[CH:16]([C:18]1[N:22]([CH3:23])[N:21]=[CH:20][C:19]=1[C:24]#[C:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1)=[O:17].Cl>O>[OH:17][CH2:16][C:18]1[N:22]([CH3:23])[N:21]=[CH:20][C:19]=1[C:24]#[C:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21225700DiisobutylaluminumhydrideHCID 86684885HCID 86684885, compound

Product 1

HCID 86684887HCID 86684887, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, 1.0 M diisobutylaluminum hydride (1.70 mL, toluene solution) was added dropwise to a tetrahydrofuran (5.0 mL) solution of 4-[(5-formyl-1-methyl-1H-pyrazol-4-yl)ethynyl]benzenesulfonamide (160 mg) at −78° C., and the obtained solution was then stirred for 1 hour. Thereafter, water was added to the reaction solution, and the obtained solution was converted to an acidic solution by addition of 2 M hydrochloric acid. Then, the solution was extracted with ethyl acetate. The organic layer was washed with water, and was then dried over anhydrous sodium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, chloroform/methanol=99:1 to 95:5), so as to obtain the title compound (60 mg) in the form of a light yellow solid.

Workup

  1. extractionThen, the solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by vacuum concentration
  5. customThe residue was purified by column chromatography (silica gel cartridge, chloroform/methanol=99:1 to 95:5)

Sources & evidence

ORD record
ord-80af704518fd493bbcffcf59ca18e2d9
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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