Dimethylformamide dimethyl acetate → HCID 131734398, compound
Reaction equation
[CH3:1][C:2]1([CH3:37])[CH2:11][C:10]2[N:9]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:21][CH2:20][CH2:19]4)=[CH:14][CH:13]=3)[C:7]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:6][C:5]=2[C:4](=[O:36])[CH2:3]1.CC(C)C(O)=O.[CH3:44][N:45]([CH3:48])[CH:46]=O>>[C:25]([O:24][C:23](=[O:29])[NH:22][C:18]1([C:15]2[CH:14]=[CH:13][C:12]([C:8]3[C:7]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:6][C:5]4[C:4](=[O:36])[C:3](=[CH:44][N:45]([CH3:48])[CH3:46])[C:2]([CH3:37])([CH3:1])[CH2:11][C:10]=4[N:9]=3)=[CH:17][CH:16]=2)[CH2:21][CH2:20][CH2:19]1)([CH3:26])([CH3:27])[CH3:28]Participants
Conditions
- Temperature
- 100 °C
Procedure
Tert-butyl (1-(4-(7,7-dimethyl-5-oxo-3-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)phenyl)cyclobutyl)carbamate (1 g, 2 mmol) was dissolved in 10 ml of anhydrous N,N-dimethylfomamide dimethylformamide dimethyl acetate. The resulting mixture was heated to 100° C. under a nitrogen atmosphere for 48 hours. TLC and LC-MS analysis showed complete consumption of the starting material. The reaction mixture was concentrated to dryness under reduced pressure. The crude residue was slurried in n-hexane (10 ml) for 1 hour. The suspension was filtered and the solid was dried until constant weigh to give the desired product as a bright yellow solid (420 mg, 76% yield). LCMS (Method A): RT=8.51 min, M+H+=552; RT=8.81 min, M+H+=525 (tert-butyl(1-(4-(6-(hydroxymethylene)-7,7-dimethyl-5-oxo-3-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)cyclobutyl)carbamate.
Workup
- customconsumption of the starting material
- concentrationThe reaction mixture was concentrated to dryness under reduced pressure
- filtrationThe suspension was filtered
- customthe solid was dried
Sources & evidence
- ORD record
- ord-8c959299b7b14a34acf5d4865c4ba300
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221838B2
Reaction notes
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