Methylamine → HCID 178485220, compound

HRID 1822121Notes

Reaction equation

HRID 1822121 reaction equation
CS[C:3]([N:14]1[CH2:18][CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[N:15]1)=[N:4][S:5]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)(=[O:7])=[O:6].[CH3:32][NH2:33]>CO>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:16]2[CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][N:14]([C:3]([NH:33][CH3:32])=[N:4][S:5]([N:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)(=[O:7])=[O:6])[N:15]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 690559963-(4-chlorophenyl)-N-((piperidin-1-yl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidothioic acid methyl ester

Product 1

HCID 178485220HCID 178485220, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a cooled mixture (<0° C.) of 3-(4-chlorophenyl)-N-((piperidin-1-yl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidothioic acid methyl ester (10.0 gram, 21 mmol) in methanol (75 mL) is added cold methylamine (15 mL). The resulting mixture is allowed to attain room temperature and stirred for 3 hours at 50° C. After cooling to room temperature the mixture is concentrated in vacuo, dissolved in dichloromethane, washed twice with water, dried over Na2SO4, filtered and concentrated in vacuo. Subsequent flash chromatography (EtOAc/MeOH/NH4OH (25% aq.)=95/5/0.5 (v/v)), followed by recrystallisation from diisopropyl ether gives 3-(4-chlorophenyl)-N-methyl-4-phenyl-N′-((piperidin-1-yl)sulfonyl)-4,5-dihydro-1H-pyrazole-1-carboxamidine (7.87 gram, 81% yield) as a white solid. MP: 175-177° C.

Workup

  1. customto attain room temperature
  2. temperatureAfter cooling to room temperature the mixture
  3. concentrationis concentrated in vacuo
  4. dissolutiondissolved in dichloromethane
  5. washwashed twice with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customSubsequent flash chromatography (EtOAc/MeOH/NH4OH (25% aq.)=95/5/0.5 (v/v)), followed by recrystallisation from diisopropyl ether

Sources & evidence

ORD record
ord-1aef38e552d74f90a885daff359cc408
Source dataset
uspto-grants-2009_10
Patent number
US07608718B2

Reaction notes

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