Monomethylamine methanol → HCID 57499603, compound

HRID 655667Notes

Reaction equation

HRID 655667 reaction equation
CO.[CH3:3][NH2:4].C(O[C:8]([C:10]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([C:25]3[C:33]4[CH:32]=[CH:31][S:30][C:29]=4[CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)[N:12]([CH2:34][CH:35]=[CH2:36])[N:11]=1)=[O:9])C>CO>[CH3:3][NH:4][C:8]([C:10]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][N:22]([C:25]3[C:33]4[CH:32]=[CH:31][S:30][C:29]=4[CH:28]=[CH:27][CH:26]=3)[CH2:23][CH2:24]2)[N:12]([CH2:34][CH:35]=[CH2:36])[N:11]=1)=[O:9]

Participants

4

Reactant 2

HCID 57454252Monomethylamine methanolHCID 57499604HCID 57499604, compound

Product 1

HCID 57499603HCID 57499603, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

40% methylamine methanol solution (5 ml) was added to a methanol solution (5 ml) of 1-allyl-5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1H-pyrazole-3-carboxylic acid ethyl ester (0.5 g, 1.1 mmol) and the mixture was stirred at room temperature for 3 days. The solution was concentrated under reduced pressure and the residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=5:1→0:1). The purified product was concentrated under reduced pressure and the residue was recrystallized from a solvent mixture of ethyl acetate-diisopropylether to obtain 1-allyl-5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1H-pyrazole-3-carboxylic acid methylamide (0.32 μg, 67% yield) as white powder.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=5:1→0:1)
  3. concentrationThe purified product was concentrated under reduced pressure
  4. customthe residue was recrystallized from a solvent mixture of ethyl acetate-diisopropylether

Sources & evidence

ORD record
ord-ec927aebd4ad4fb192ed17bdf21be404
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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