Hydrochloric Acid → Dapivirine

HRID 1363888ノート

反応式

HRID 1363888 の反応式
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

参加物

7

反応物 5

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

生成物 1

HCID 214347Dapivirine収率 86%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
42.5 °C

実験手順

A mixture of intermediate 14 (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 (comp. 17).

後処理

  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
  11. filtration(100 ml), filtered off
  12. washwashed with ethanol (50 ml)
  13. customdried

出典と根拠

ORDレコード
ord-6a8de9aaf9fa438396d0a0e264acc5ae
出典データセット
uspto-grants-2011_02
特許番号
US07887845B2

反応ノート

読み込み中…