Triethylamine → HCID 69222621, compound
Reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16]([OH:18])=[O:17])[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:29]([NH:33][CH3:34])[CH:30]([CH3:32])[CH3:31]>C1COCC1>[CH2:29]([N:33]([CH3:34])[C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16]([OH:18])=[O:17])[CH:9]=2)=[CH:4][CH:3]=1)[CH:30]([CH3:32])[CH3:31]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
In a pressure tube, 200 mg (0.64 mmol) of 3-[5-(6-chloro-pyridin-3-yl)-isoxazol-3-yl]-benzoic acid, 97 mg (0.96 mmol, 1.5 eq.) of triethyl amine and 166 mg (1.9 mmol, 3.0 eq.) of isobutyl-methyl-amine are dissolved in 3 ml of THF. The reaction mixture is heated to 120° C. and after 6 h to 150° C. After 60 h, the mixture is cooled to room temperature and the solvent is removed. After addition of 10 ml of water, the pH is adjusted to 2 and the precipitate filtered off. The solid is then dissolved in 10 ml of methanol and 5 ml of dichloroethane, precipitated through addition of 10 ml of hexane and filtered. Recrystallisation from 15 ml of dichloromethane and 1 ml of methanol yields the title compound as a white solid. Mass spectrum: m/z (M+H)+: 352.2
Workup
- temperaturethe mixture is cooled to room temperature
- customthe solvent is removed
- additionAfter addition of 10 ml of water
- filtrationthe precipitate filtered off
- dissolutionThe solid is then dissolved in 10 ml of methanol
- custom5 ml of dichloroethane, precipitated through addition of 10 ml of hexane
- filtrationfiltered
- customRecrystallisation from 15 ml of dichloromethane and 1 ml of methanol
Sources & evidence
- ORD record
- ord-ccd2abda2c9e4bab88863306cc968d5c
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432293B2
Reaction notes
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