Dimethylformamide → 3-Chloro-N-(1-(2-(3,3-dimethylbutanamido)ethyl)-1H-tetrazol-5-yl)benzamide

반응식

[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[N:12]([CH2:13][CH2:14]C)[N:11]=[N:10][N:9]=1)=[O:6].[C:19](OC(=O)NCCBr)([CH3:22])([CH3:21])[CH3:20].[CH3:30][CH2:31][N:32](CC)CC.CN(C=[O:41])C>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[N:12]([CH2:13][CH2:14][NH:32][C:31](=[O:41])[CH2:30][C:19]([CH3:20])([CH3:21])[CH3:22])[N:11]=[N:10][N:9]=1)=[O:6]

참가 물질

반응물 4

HCID 6228Dimethylformamide

HCID 8471Triethylamine

HCID 9657943-Chloro-N-(1-propyl-1H-tetrazol-5-yl)benzamide

HCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

생성물 1

HCID 904081113-Chloro-N-(1-(2-(3,3-dimethylbutanamido)ethyl)-1H-tetrazol-5-yl)benzamide수율 42%

실험 절차

Compound (A) (250 mg; 1.12 mmol), Compound (B) (250 mg; 1.12 mmol) and 340 mg (3.36 mmol) of Et3N were added to a round bottomed flask containing 15 ml of DMF and refluxed overnight (about 18 hours). The reaction mixture was evaporated to dryness under reduced pressure and 20 ml of H2O added. This aqueous phase was extracted with CH2Cl2 (3×30 ml) and the organic layers combined, dried over MgSO4 and further concentrated. The crude product obtained was purified over silica gel and eluted with CHCl3. To provide a brown oil in 42% yield.