3,5-Dibromopyridine → (1S,5S)-benzyl 6-(5-bromopyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

HRID 1817008노트

반응식

HRID 1817008 반응식
[C@@H:1]12[CH2:7][NH:6][C@@H:5]1[CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2]2.[Br:18][C:19]1[CH:20]=[N:21][CH:22]=[C:23](Br)[CH:24]=1>>[Br:18][C:19]1[CH:24]=[C:23]([N:6]2[CH2:7][C@@H:1]3[C@H:5]2[CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:2]3)[CH:22]=[N:21][CH:20]=1

참가 물질

3

반응물 2

HCID 693693,5-DibromopyridineHCID 23635906benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

생성물 1

HCID 23635294(1S,5S)-benzyl 6-(5-bromopyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate수율 47%

실험 절차

The product of Example 52D (230 mg, 1.0 mmol) and 3,5-dibromopyridine were processed as described in Example 1E. The crude product was purified by chromatography (SiO2, ethyl acetate, Rf 0.2) to provide the title compound (180 mg, 47% yield). 1H NMR (MeOH-d4, 300 MHz) δ 3.20 (dd, J=12.5, 4.0 Hz, 1H), 3.30 (m, 2H), 3.40 (m, 1H), 3.64 (dd, J=7.8, 3.4 Hz, 1H), 3.95-4.10 (m, 3H), 4.75 (m, 1H), 5.15 (m, 2H), 7.05 (t, J=2.1 Hz, 1H), 7.24 (m, 3H), 7.35 (m, 2H), 7.70 (d, J=2.3 Hz, 1H), 7.93 (d, J=1.7 Hz, 1H); MS (DCI/NH3) m/z 390 (M+2+H)+, 388 (M+H)+.

후처리

  1. customThe crude product was purified by chromatography (SiO2, ethyl acetate, Rf 0.2)

출처 및 근거

ORD 기록
ord-bd89eb797e4a49d381cb4bb3e04179e3
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598236B2

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