4-Methylmorpholine → 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N-[4-(1,1-dioxoisothiazolidin-2-yl)phenyl]valeramide
Reaction equation
CN1CCOCC1.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH2:17][S:16]2(=[O:21])=[O:20])=[CH:11][CH:10]=1.[CH3:22][C:23]1[O:27][N:26]=[C:25]([C:28]2[CH:29]=[C:30]([CH:39]=[CH:40][CH:41]=2)[O:31][CH:32]([CH2:36][CH2:37][CH3:38])[C:33](O)=[O:34])[N:24]=1.Cl.CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1>CN(C=O)C.O>[CH3:22][C:23]1[O:27][N:26]=[C:25]([C:28]2[CH:29]=[C:30]([CH:39]=[CH:40][CH:41]=2)[O:31][CH:32]([CH2:36][CH2:37][CH3:38])[C:33]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:19][CH2:18][CH2:17][S:16]3(=[O:21])=[O:20])=[CH:13][CH:14]=2)=[O:34])[N:24]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
101 μl (1.00 mmol) of 4-methylmorpholine are added to a solution of 212 mg (1.00 mmol) of 2-(4-aminophenyl)isothiazolidine 1,1-dioxide, 276 mg (1.00 mmol) of 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-pentanoic acid, 192 mg (1.00 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) and 135 mg (1.00 mmol) of hydroxybenzotriazole hydrate (HOBt) in 1 ml of DMF, and the mixture is stirred at room temperature for 24 hours. The reaction mixture is introduced into water, and the precipitate is filtered off, giving 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N-[4-(1,1-dioxoisothiazolidin-2-yl)phenyl]valeramide as a colourless solid; ESI 471.
Workup
- filtrationthe precipitate is filtered off
Sources & evidence
- ORD record
- ord-a9ed98e55e02492cbf9274f924ef84e1
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199133B2
Reaction notes
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