1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-(5-(3,4-Diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-2-one
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[C:7]([OH:9])=O)[CH3:2].CC[N:18]=[C:19]=[N:20]CCCN(C)C.[CH:27]1[CH:28]=[CH:29][C:30]2N(O)N=[N:33][C:31]=2[CH:32]=1.[O:37]1CCO[CH2:39][CH2:38]1>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:7]2[O:9][N:18]=[C:19]([C:27]3[CH:32]=[C:31]4[C:30]([CH2:39][C:38](=[O:37])[NH:33]4)=[CH:29][CH:28]=3)[N:20]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH3:2]Participants
5
Procedure
To a stirred solution of 3,4-diethoxybenzoic acid (73 mg, 0.35 mmol) in 1,4-dioxane was added EDCI (87 mg, 0.45 mmol) and HOBt (62 mg, 0.45 mmol), the reaction was stirred 20 min at room temperature. To the reaction was added the N′-hydroxyimidamide (87 mg, 0.45 mmol) and the mixture was stirred for 30 min at room temperature followed by 16 h at 95° C. The reaction was concentrated under reduced pressure, diluted with EtOAc (80 ml) and washed with brine (2×30 ml). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by column chromatography using CH2Cl2:MeOH (9:1) to offer the product as a pale yellow solid 50% yield (64 mg, 0.175 mmol). MS (EI) m/z: 366 (M+)
Workup
- stirringthe mixture was stirred for 30 min at room temperature
- waitfollowed by 16 h at 95° C
- concentrationThe reaction was concentrated under reduced pressure
- additiondiluted with EtOAc (80 ml)
- washwashed with brine (2×30 ml)
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe crude was purified by column chromatography
Sources & evidence
- ORD record
- ord-fc9d1dc2236345ca8ee96267a1604eab
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481573B2
Reaction notes
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