Water → Depyrazine 7,8-Dinitrophenyl Varenicline

HRID 10087노트

반응식

HRID 10087 반응식
[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]

참가 물질

6

반응물 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

생성물 1

HCID 9878181Depyrazine 7,8-Dinitrophenyl Varenicline

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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 methanol (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% methanol/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+).

후처리

  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
  9. customto provide brown solids

출처 및 근거

ORD 기록
ord-bcb560618ed647df924c3601e43a5253
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091372B2

반응 노트

불러오는 중…