Water → Depyrazine 7,8-Dinitrophenyl Varenicline

HRID 2182779ノート

反応式

HRID 2182779 の反応式
[N+:1]([C:4]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]2[CH:11]3[CH2:18][CH:7]([CH2:8][N:9](C(=O)C(F)(F)F)[CH2:10]3)[C:6]=2[CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Na+].[Na+].O>CO>[N+:15]([C:14]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]2[CH:7]3[CH2:18][CH:11]([CH2:10][NH:9][CH2:8]3)[C:12]=2[CH:13]=1)([O-:17])=[O:16]

参加物

5

反応物 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 218647441-(7,8-Dinitro-1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)-2,2,2-trifluoroethan-1-one

生成物 1

HCID 9878181Depyrazine 7,8-Dinitrophenyl Varenicline収率 71.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

1-(4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (3.7 g, 10.7 mmol) and Na2CO3 (2.3 g, 21.4 mmol) were combined in MeOH (50 mL) and H2O (20 mL) then warmed to reflux for 18 hours. The reaction was cooled, concentrated, treated with H2O and extracted with CH2Cl2 (3×50 mL) then dried through a cotton plug. After concentration, the residue was chromatographed to provide brown solids (1.9 g, 71%) (TLC 5% MeOH/CH2Cl2 (NH3) Rf 0.36). 1H NMR (400 MHz, CDCl3) δ 7.69 (s, 2H), 3.17 (br s, 2H), 3.11 (d, J=12.6 Hz, 2H), 2.53 (m, 1H), 2.07 (d, J=11.0 Hz, 1H). GCMS m/e 249 (M+).

後処理

  1. temperatureto reflux for 18 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. additiontreated with H2O
  5. extractionextracted with CH2Cl2 (3×50 mL)
  6. customthen dried through a cotton plug
  7. concentrationAfter concentration
  8. customthe residue was chromatographed

出典と根拠

ORDレコード
ord-b6c6cc73f2f4492097aee5c13b96c12b
出典データセット
uspto-grants-2005_05
特許番号
US06897310B2

反応ノート

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