1,1'-Carbonyldiimidazole → [3-(4-Ethylphenyl)-5-(3-isopropoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl](4-hydroxypiperidin-1-yl)-methanone
Reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([N:17]3[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]3)=[O:16])[CH2:12][CH:11]([C:24]([OH:26])=O)[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O[N:40]=[C:41]([O:43][CH:44]([CH3:46])[CH3:45])[NH2:42]>CN(C=O)C.O1CCOCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:10][CH:11]([C:24]3[O:26][N:42]=[C:41]([O:43][CH:44]([CH3:46])[CH3:45])[N:40]=3)[CH2:12][N:13]([C:15]([N:17]3[CH2:18][CH2:19][CH:20]([OH:23])[CH2:21][CH2:22]3)=[O:16])[CH2:14]2)=[CH:7][CH:8]=1)[CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 80.0 mg (0.222 mmol) of the carboxylic acid from Example 21A in 0.89 ml of DMF and 1.78 ml of 1,4-dioxane were added, at 60° C., 108 mg (0.666 mmol) of 1,1′-carbonyldiimidazole, and the mixture was stirred for 3 h. Subsequently, the mixture was admixed with 52.4 mg (0.333 mmol; 75% purity) of isopropyl N′-hydroxyimidocarbamate [G. Zinner, G. Nebel, Arch. Pharm. 1970, 303, 385-390] and then stirred at RT for 2 h and then at 120° C. for 2 h. The reaction solution was concentrated under reduced pressure and purified directly by means of preparative HPLC. Yield: 22.6 mg (22% of theory)
Workup
- waitat 120° C. for 2 h
- concentrationThe reaction solution was concentrated under reduced pressure
- custompurified directly by means of preparative HPLC
Sources & evidence
- ORD record
- ord-a59b2d5a91534eeeb61f4f39f1e1fc78
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084469B2
Reaction notes
Loading…