Hydrochloric Acid → Dapivirine

HRID 1070948노트

반응식

HRID 1070948 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[CH:5]=[CH:4][N:3]=1.Cl.CC(O)C.[NH2:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=1.C([O-])(O)=O.[Na+]>O>[CH3:17][C:10]1[CH:11]=[C:12]([CH3:16])[CH:13]=[C:14]([CH3:15])[C:9]=1[NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)[N:7]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 133964-AminobenzonitrileHCID 516892Sodium BicarbonateHCID 223984242-Chloro-N-(2,4,6-trimethylphenyl)-4-pyrimidinamine

생성물 1

HCID 214347Dapivirine수율 86%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
42.5 °C

실험 절차

A mixture of intermediate 49 (0.082 mol) and 5.4 N HCl in 2-propanol (0.086 mol) in water (300 ml) was stirred and warmed to 40-45° C. over 30 minutes, 4-Amino-benzonitrile (0.242 mol) was added at 40-45° C. The reaction mixture was stirred and refluxed for 4.5 hours, then cooled to room temperature. The mixture was alkalized by portionwise addition of NaHCO3. This mixture was extracted with ethylacetate. The organic layer was separated, washed with brine, dried, filtered and the solvent was evaporated. This fraction was stirred in ethanol p.a. (100 ml), filtered off, washed with ethanol (50 ml), then dried, yielding 23.1 g (86%) 4-[[4-[(2,4,6-trimethylphenyl)-amino]-2-pyrimidinyl]amino]benzonitrile (compound 52).

후처리

  1. stirringThe reaction mixture was stirred
  2. temperaturerefluxed for 4.5 hours
  3. temperaturecooled to room temperature
  4. extractionThis mixture was extracted with ethylacetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. stirringThis fraction was stirred in ethanol p.a
  11. filtration(100 ml), filtered off
  12. washwashed with ethanol (50 ml)
  13. customdried

출처 및 근거

ORD 기록
ord-9f0747e17d834161a6e2d406ff3ffe02
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903213B2

반응 노트

불러오는 중…