3-Bromopyridine → tert-butyl (1S,4S)-5-(3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

HRID 914745

반응식

[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Br[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1>>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([N:5]2[CH2:6][C@@H:1]3[CH2:7][C@H:4]2[CH2:3][N:2]3[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:17]=1

참가 물질

반응물 2

HCID 122863-Bromopyridine

HCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

생성물 1

HCID 16748710tert-butyl (1S,4S)-5-(3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate수율 99%

실험 절차

tert-Butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate, prepared as described in J. Med. Chem., (1988) 31, 1598-1611, and 3-bromopyridine (Aldrich Chemical Company) were processed as described in Example 1A to provide the title compound (99% yield). 1H NMR (CDCl3, 300 MHz) δ 1.42 (s, 4.5H), 1.48 (s, 4.5H), 1.91-2.03 (m, 2H),3.14 (d, J=14.7 Hz, 0.5H), 3.23 (d, J=14.7 Hz, 0.5H), 3.37-3.48 (m, 2H), 3.60 (d, 8.45 Hz, 1H), 4.41 (s, 1H), 4.53 (s, 0.5H), 4.67 (s, 0.5H), 6.85 (dd, J=2.94, 8.83 Hz, 1H), 7.09-7.21 (m, 1H), 7.95-8.06 (m, 2H); MS (DCI/NH3) m/z 276 (M+H)+.

출처 및 근거

ORD 기록: ord-18fae8ab085a4e33a44b32399dda86ae
출처 데이터셋: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07265115B2

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