Reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[O:23]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[NH:26][CH2:25][CH:24]1[C:33]([O-:35])=O.[Li+].C(N(CC)CC)C.[CH3:44][C:45]1[N:49]=[C:48]([CH2:50][NH2:51])[O:47][N:46]=1>ClCCl.CN(C=O)C.C(OCC)(=O)C>[CH3:44][C:45]1[N:49]=[C:48]([CH2:50][NH:51][C:33]([CH:24]2[O:23][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[NH:26][CH2:25]2)=[O:35])[O:47][N:46]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
HOBT (1.0 g, 6.5 mmol) and WSC.HCl (1.1 g, 5.8 mmol) were added to a solution of lithium benzomorpholine-2-carboxylate (900 mg, 5.0 mmol) in dichloromethane (25 ml) and DMF (4.0 ml) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 45 min. Triethylamine (0.73 ml, 530 mg, 5.2 mmol) and a solution of 3-methyl-1,2,4-oxadiazol-5-ylmethylamine (590 mg, 5.2 mmol, prepared according to H. Biere et al., Liebigs Ann. Chem. 1749 (1986)) in dichloromethane (5.0 ml) were added and the mixture was stirred for 18 h. The mixture was reduced, taken up in ethyl acetate and washed with 0.3N potassium hydrogen sulphate, saturated sodium hydrogen carbonate and brine. The organic phase was dried and reduced. Chromatography (80% ethyl acetate/20% 60-80 petroleum ether) afforded N-(3-methyl-1,2,4-oxadiazol-5-ylmethyl)benzomorpholine-2-carboxamide (900 mg, 65%) as a brown gum.
Workup
- temperaturewhile cooling in an ice/water bath
- stirringthe mixture was stirred for 18 h
- washwashed with 0.3N potassium hydrogen sulphate, saturated sodium hydrogen carbonate and brine
- customThe organic phase was dried
Sources & evidence
- ORD record
- ord-edd93d841a5f459c9ad614d62d070ad2
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365065B2
Linked notes
Loading…