4-Methylmorpholine → 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N-[4-(2-oxopiperidin-1-yl)phenyl]-2-phenylacetamide
Reaction equation
CN1CCOCC1.[CH3:8][C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:15]=[C:16]([CH:28]=[CH:29][CH:30]=2)[O:17][CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([OH:21])=O)[N:10]=1.[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][C:39]2=[O:44])=[CH:34][CH:33]=1.Cl.CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH3:8][C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:15]=[C:16]([CH:28]=[CH:29][CH:30]=2)[O:17][CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][C:39]3=[O:44])=[CH:34][CH:33]=2)=[O:21])[N:10]=1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
35 μl (0.322 mmol) of 4-methylmorpholine are added to a solution of 100 mg (0.322 mmol) of [3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxyl]-2-phenylacetic acid, 61.3 mg (0.322 mmol) of 1-(4-aminophenyl)piperidin-2-one (prepared from 1-(4-nitrophenyl)piperidin-2-one by hydrogenation using Raney nickel as catalyst), 61.7 mg (0.322 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) and 49.3 mg (0.322 mmol) of hydroxybenzotriazole hydrate (HOBt) in 3 ml of DMF, and the mixture is stirred at room temperature for 48 hours. The reaction mixture is introduced into aqueous sodium carbonate solution, and the precipitate is filtered off, giving 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N-[4-(2-oxopiperidin-1-yl)phenyl]-2-phenylacetamide as a colourless solid; ESI 483.
Workup
- filtrationthe precipitate is filtered off
Sources & evidence
- ORD record
- ord-fb07ee39302a4655b02908ee5acfc4b6
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07273867B2
Reaction notes
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