Triethylamine → HCID 89709123, compound

HRID 1526203Notes

Reaction equation

HRID 1526203 reaction equation
CC1[N:3]([C:8]2[CH:12]=[C:11]([C:13]3[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH:18]=3)[N:10]([CH3:20])[N:9]=2)C(C)=CC=1.NO.Cl.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(O)C.O>[CH3:20][N:10]1[C:11]([C:13]2[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH:18]=2)=[CH:12][C:8]([NH2:3])=[N:9]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 117666790HCID 117666790, compound

Product 1

HCID 89709123HCID 89709123, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 4-[3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazol-5-yl]-1-methyl-1,2,3,6-tetrahydropyridine (1.06 g) and hydrochloric acid hydroxylamine (2.73 g) in ethanol (10 mL) and water (1 mL) was added triethylamine (1.10 mL), followed by stirring at 110° C. for 5 hours. After leaving to be cooled, the mixture was neutralized with a saturated aqueous sodium hydrogen carbonate solution, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH2 type: eluent; chloroform:methanol=100:0-98:2) to obtain 1-methyl-5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazol-3-amine (574 mg) as a pale brown solid.

Workup

  1. customAfter leaving
  2. temperatureto be cooled
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (NH2 type: eluent; chloroform:methanol=100:0-98:2)

Sources & evidence

ORD record
ord-923686eded324ae7a416b434ab5087ae
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

Loading…