Dimethylformamide → 2-[4-(4-Cyano-benzyl)-piperidin-1-yl]-2-oxo-N-(2-oxo-2,3-dihydro-benzoxazol-6-yl)-acetamide
Reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([NH:11][C:12](=[O:16])[C:13]([OH:15])=O)=[CH:10][C:4]=2[O:3]1.CN1CCOCC1.CN(C)C=O.C(OC(Cl)=O)C(C)C.Cl.[NH:38]1[CH2:43][CH2:42][CH:41]([CH2:44][C:45]2[CH:52]=[CH:51][C:48]([C:49]#[N:50])=[CH:47][CH:46]=2)[CH2:40][CH2:39]1>>[C:49]([C:48]1[CH:47]=[CH:46][C:45]([CH2:44][CH:41]2[CH2:42][CH2:43][N:38]([C:13](=[O:15])[C:12]([NH:11][C:9]3[CH:8]=[CH:7][C:5]4[NH:6][C:2](=[O:1])[O:3][C:4]=4[CH:10]=3)=[O:16])[CH2:39][CH2:40]2)=[CH:52][CH:51]=1)#[N:50]Participants
Reactant 5
Product 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of 0.3g (1.5 mmol) of N-(2-oxo-2,3-dihydro-benzoxazol-6-yl)-oxalamic acid, 0.165 ml (1.5 mmol) of N-methyl-morpholine in 8 ml of dimethylformamid 0.2 ml (1.5 mmol) of isobutyl-chloroformate is added dropwise at 0° C. and the mixture is stirred at 0° C. for 1 hour. Then 0.333 g (1.4 mmol) of 4-piperidin-4-ylmethyl-benzonitrile hydrochloride and 0.165 ml (1.5 mmol) of N-methyl-morpholine are added and the reaction mixture is stirred at 0° C. for 1 hour, at room temperature for 16 hours. The reaction mixture is concentrated and the residue is purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and toluene:methanol=4:1 as eluent to yield 0.045 g (8.0%) of the title compound. Rf.: 0.4. Melting Point: 259-260° C. (isopropanol).
Workup
- additionis added dropwise at 0° C.
- stirringthe reaction mixture is stirred at 0° C. for 1 hour, at room temperature for 16 hours
- concentrationThe reaction mixture is concentrated
- customthe residue is purified by column chromatography
Sources & evidence
- ORD record
- ord-a114bd94bb0d425ebe3d57a283900bfe
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435744B2
Reaction notes
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