Water → Depyrazine 7,8-Dinitrophenyl Varenicline

HRID 2187560ノート

反応式

HRID 2187560 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.C(Cl)Cl>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

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 21226129Dichloromethane methanolHCID 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

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-triflouroethanone (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) Rf0.36). 1H NMR (400 MHz, CDCl3) δ7.69 (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. temperaturethen warmed
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. additiontreated with H2O
  6. extractionextracted with CH2Cl2 (3×50 mL)
  7. customthen dried through a cotton plug
  8. concentrationAfter concentration
  9. customthe residue was chromatographed
  10. customto provide brown solids

出典と根拠

ORDレコード
ord-c8abf7582ecb4b2ab0b8467e63cc20e6
出典データセット
uspto-grants-2002_06
特許番号
US06410550B1

反応ノート

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