Ethyl orthoformate → tert-butyl 3-(6-bromo-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate

HRID 919645노트

반응식

HRID 919645 반응식
[NH2:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)=[CH:4][C:5]([Br:8])=[N:6][CH:7]=1.[CH:23](OCC)(OCC)OCC>>[Br:8][C:5]1[N:6]=[CH:7][C:2]2[N:1]=[CH:23][N:9]([CH:10]3[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]3)[C:3]=2[CH:4]=1

참가 물질

3

반응물 2

HCID 31214Ethyl orthoformateHCID 86706485Tert-butyl 3-((5-amino-2-bromopyridin-4-yl)amino)piperidine-1-carboxylate

생성물 1

HCID 72344680tert-butyl 3-(6-bromo-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate수율 70%

실험 절차

A mixture of tert-butyl 3-((5-amino-2-bromopyridin-4-yl)amino)piperidine-1-carboxylate (1.1 g, 3.0 mmol, 1.0 eq) in CH(OCH2CH3)3 (214 mg, 30 mmol, 10 eq) was refluxed for 40 h. Then the residual CH(OCH2CH3)3 was removed in vacuum and the crude product was purified by silica gel column chromatography with EtOAc in PE (½ v/v) to give the title compound (0.8 g, 70%) as yellow oil. 1H NMR (400 MHz, CDCl3) δ: 8.87 (s, 1H), 8.06 (s, 1H), 7.62 (s, 1H), 4.30-4.28 (m, 2H), 4.02-4.00 (m, 1H), 3.27-3.22 (m, 1H), 3.09-3.03 (m, 1H), 2.31-2.30 (m, 1H), 2.13-2.10 (m, 1H), 1.88-1.85 (m, 1H), 1.74-1.71 (m, 1H), 1.50 (s, 9H). ESI-MS (M+H+): 381.0.

후처리

  1. temperaturewas refluxed for 40 h
  2. customThen the residual CH(OCH2CH3)3 was removed in vacuum
  3. customthe crude product was purified by silica gel column chromatography with EtOAc in PE (½ v/v)

출처 및 근거

ORD 기록
ord-1170db8207e944dd85bbd0dd9171b8a2
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273028B2

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