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

HRID 1619220ノート

反応式

HRID 1619220 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6e7dbd0950534212aba9e920b8bfd5ed
出典データセット
uspto-grants-2014_07
特許番号
US08772291B2

反応ノート

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