Hydrochloric Acid → (4-Bromo-phenyl)-(8-pyrimidin-2-yl-8-aza-bicyclo[3.2.1]oct-3-yl)-methanone

HRID 1619220노트

반응식

HRID 1619220 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:23]C)=[C:9]2[CH2:15][CH:14]3[N:16]([C:17]4[N:22]=[CH:21][CH:20]=[CH:19][N:18]=4)[CH:11]([CH2:12][CH2:13]3)[CH2:10]2)=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:9]2[CH2:15][CH:14]3[N:16]([C:17]4[N:18]=[CH:19][CH:20]=[CH:21][N:22]=4)[CH:11]([CH2:12][CH2:13]3)[CH2:10]2)=[O:23])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 687002943-[(4-Bromo-phenyl)-methoxy-methylene]-8-pyrimidin-2-yl-8-aza-bicyclo[3.2.1]octane

생성물 1

HCID 68699864(4-Bromo-phenyl)-(8-pyrimidin-2-yl-8-aza-bicyclo[3.2.1]oct-3-yl)-methanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-[(4-bromo-phenyl)-methoxy-methylene]-8-pyrimidin-2-yl-8-aza-bicyclo[3.2.1]octane (2.44 g, 6.32 mmol), aqueous HCl (10.5 ml, 6N) and THF (50 ml) was stirred at room temperature overnight. The mixture was added by saturated aq. NaHCO3 until bubbling was gone. The mixture was diluted with ethyl acetate and the organic phase was dried over MgSO4 and concentrated. ISCO was used to do purification and (4-bromo-phenyl)-(8-pyrimidin-2-yl-8-aza-bicyclo[3.2.1]oct-3-yl)-methanone was obtained as white solid (2.16 g, 92%). MS (M+1)=374. 1H NMR (CDCl3) 8.33 (d, J=12 Hz 2H), 7.84 (d, J=13 Hz 2H), 7.62 (d, J=13 Hz 2H), 6.51 (t, J=12 Hz 1H), 4.87 (m, 2H), 3.90 (m, 1H), 2.23 (m, 2H), 2.08 (m, 2H), 1.97 (m, 2H), 1.72 (m, 2H).

후처리

  1. customuntil bubbling
  2. additionThe mixture was diluted with ethyl acetate
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. custompurification

출처 및 근거

ORD 기록
ord-6e7dbd0950534212aba9e920b8bfd5ed
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772291B2

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