2-Acetoxyisobutyroyl chloride → HCID 59618691、化合物
反応式
[OH:1]/[N:2]=[C:3](\[NH2:38])/[CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:14][C:13]3[N:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=[CH:18][C:12]=3[CH2:11][N:10]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:9]=2[CH:37]=1.C([O:42][C:43]([CH3:48])([CH3:47])[C:44](Cl)=O)(=O)C>N1C=CC=CC=1>[F:36][C:33]([F:35])([F:34])[O:32][C:29]1[CH:30]=[CH:31][C:26]([S:23]([N:10]2[C:9]3[CH:37]=[C:5]([CH2:4][C:3]4[N:38]=[C:44]([C:43]([OH:42])([CH3:48])[CH3:47])[O:1][N:2]=4)[CH:6]=[CH:7][C:8]=3[NH:14][C:13]3[N:15]=[C:16]([C:19]([F:21])([F:22])[F:20])[CH:17]=[CH:18][C:12]=3[CH2:11]2)(=[O:25])=[O:24])=[CH:27][CH:28]=1参加物
4
反応条件
- 温度
- 82 °C
実験手順
To a solution of (1Z)-N′-hydroxy-2-[6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]ethanimidamide (92 mg, 0.163 mmol, the product of Step A) in pyridine was added 2-acetoxyisobutyryl chloride (0.268 g, 1.63 mmol). The resulting mixture was heated at 80-84° C. for 1.5 hr, until LC-MS indicated the reaction was complete, and then the solution was concentrated to remove pyridine. The bright orange residue was dissolved in 5 mL of MeOH and K2CO3 was added. The mixture was stirred for 2 hr at 50° C., then another 0.5 g of K2CO3 was added and the solution was stirred for another 2 hr. The solution was filtered to remove solids and the filtrate was concentrated to remove MeOH. The residue was purified by column chromatography on silica gel, eluting with hexane/ethyl acetate (3:1-2:1) to give the title compound; Mass Spectrum: m/e=630 (M+1).