반응식
[B:1](OC(C)C)([O:6]C(C)C)[O:2]C(C)C.Br[C:15]1[CH:20]=[CH:19][C:18]([S:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C([Li])CCC.O>O1CCCC1>[CH3:30][N:27]1[CH2:28][CH2:29][N:24]([S:21]([C:18]2[CH:19]=[CH:20][C:15]([B:1]([OH:6])[OH:2])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[CH2:25][CH2:26]1참가 물질
반응 조건
- 온도
- -78 °C
실험 절차
Triisopropyl borate (0.64 mL, 2.8 mmol) was added to a solution of 1-[(4-bromophenyl)sulfonyl]-4-methylpiperazine (0.602 g, 1.9 mmol; described: in Keasling, H. H. et el. J. Med. Chem. 1965, 8, 548-550) in anhydrous tetrahydrofuran (7 mL) at −78° C. under a nitrogen atmosphere followed by dropwise addition of n-butyllithium (1.4 mL, 2.2 mmol). The resulting mixture was stirred at −78° C. for 2 h and at room temperature for another 16 h. Water (2.0 mL) was added and the mixture stirred for 30 min and evaporated to dryness. The residue was pre-adsorbed onto silica and purified by column chromatography on silica using methylene chloride/methanol, (9:1 to 1:9), as the eluent. The product was re-crystallized from water to give 311 mg (58% yield) of the title compound as white crystals: mp 215-218° C.; 1H NMR (DMSO-d6, 400 MHz) δ 8.47 (br s, 2H), 8.05 (d, J=8 Hz, 2H), 7.73 (d, J=8 Hz, 2H), 3.77 (m, 2H), 3.40 (m, 2H), 3.13 (m, 2H), 2.71 (s, 3H), 2.65 (m, 2H); 13C NMR (DMSO-d6, 100 MHz) δ 133.7, 133.3, 124.7, 49.8, 41.6, 41.4; MS (TSP) m/z 285 (M++1).
후처리
- stirringthe mixture stirred for 30 min
- customevaporated to dryness
- custompurified by column chromatography on silica
- customThe product was re-crystallized from water
출처 및 근거
- ORD 기록
- ord-f6b966f149514d3181a69c0dfc257fa4
- 출처 데이터셋
- uspto-grants-2009_09
- 특허 번호
- US07595321B2
연결된 노트
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