Methanol → HCID 68410858, compound

HRID 2194731Notes

Reaction equation

HRID 2194731 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=2)=[CH:11][C:10]([CH:21]=O)=[N:9]1.[CH3:23][NH2:24].CO.CO.[BH4-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=2)=[CH:11][C:10]([CH2:21][NH:24][CH3:23])=[N:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 86631686HCID 86631686, compound

Product 1

HCID 68410858HCID 68410858, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-chlorophenyl)-5-[(6-methylpyridin-2-yl)thio]-1H-pyrazole-3-carbaldehyde (415 mg) in tetrahydrofuran (4 mL) were added 40% methylamine-methanol solution (1.5 mL) and methanol (4 mL) at 0° C., and the mixture was stirred at room temperature for 4 hr. Sodium borohydride (905 mg) was added to the reaction mixture at 0° C. and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound as a yellow oil (yield 450 mg, yield quantitative).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7ce634f6dea4390aa916eb2b9d52533
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

Loading…