Reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21]([NH:23][CH:24]4[CH2:26][CH2:25]4)=[O:22])[CH:15]=3)=[CH:10][CH:9]=2)=[N:5][N:4]=1.[I-].[K+].CN(C=O)C.[NH:34]1[CH2:39][CH2:38][S:37][CH2:36][CH2:35]1>>[CH:24]1([NH:23][C:21]([C:16]2[CH:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:6]4[O:7][C:3]([CH2:2][N:34]5[CH2:39][CH2:38][S:37][CH2:36][CH2:35]5)=[N:4][N:5]=4)=[CH:9][CH:10]=3)[C:19]([CH3:20])=[CH:18][CH:17]=2)=[O:22])[CH2:26][CH2:25]1Participants
5
Reactant 4
Product 1
Procedure
4′-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 45) (37 mg) and potassium iodide (5 mg) were mixed in thiomorpholine (2 ml) and DMF (2 ml) and the reaction stirred at room temperature for 18 hours. The solvents were evaporated under vacuum and the residue purified by bond-elut (silica), eluting with an ethyl acetate/cyclohexane gradient. After evaporation of the solvent this gave N-cyclopropyl-6-methyl-4′-[5-(thiomorpholin-4-ylmethyl)-1,3,4-oxadiazol-2-yl]-1,1′-biphenyl-3-carboxamide.
Workup
- customThe solvents were evaporated under vacuum
- customthe residue purified by bond-elut (silica)
- washeluting with an ethyl acetate/cyclohexane gradient
- customAfter evaporation of the solvent this gave N-cyclopropyl-6-methyl-4′-[5-(thiomorpholin-4-ylmethyl)-1,3,4-oxadiazol-2-yl]-1,1′-biphenyl-3-carboxamide
Sources & evidence
- ORD record
- ord-0408fa70f4a3405f9db5e9fa86ea2549
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07425555B2
Linked notes
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