Ammonia → Sumatriptan

HRID 651717

反応式

HRID 651717 の反応式
[Ca].N.C([N:10]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][S:20]([N:23](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:24])(=[O:22])=[O:21])=[CH:16][CH:17]=2)[C:12]([CH2:38][CH2:39][N:40]([CH3:42])[CH3:41])=[CH:11]1)C1C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1.O>[CH3:42][N:40]([CH3:41])[CH2:39][CH2:38][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([CH2:19][S:20]([NH:23][CH3:24])(=[O:21])=[O:22])[CH:14]=2)[NH:10][CH:11]=1

参加物

7

反応物 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5460341CalciumHCID 217091161-[1-benzyl-3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-diphenylmethyl-N-methylmethanesulfonamide

生成物 1

HCID 5358Sumatriptan収率 56.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred slurry of calcium turnings (243 mg, 6 mmol) in tetrahydrofuran (4 ml) at −40° C. was condensed liquid ammonia (4 ml). The blue bronze was stirred at −50 to −40° C. for a further 15 min, before a solution of 1-[1-benzyl-3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-diphenylmethyl-N-methylmethanesulfonamide (from step (e), 836 mg, 1.5 mmol) in tetrahydrofuran (2 ml) was added dropwise, maintaining the temperature below −40° C. The dark blue solution was stirred at −40° C. for a further 30 minutes, before saturated ammonium chloride solution (10 ml) was added dropwise and the grey solution warmed to ambient temperature. Water (10 ml) was then added and the white slurry stirred for 15 min, before being filtered in vacuo. The solid was then dissolved in 5N HCl (12 ml) and the resulting orange solution extracted with ethyl acetate (10 ml). The pH of the aqueous phase was then adjusted (pH=10) with 10N NaOH which resulted in precipitation. The solid was filtered and dried in vacuo at 50° C. overnight to yield the title compound (250 mg, 56%) as a white solid. m.p. 159-163° C.

後処理

  1. customat −40° C.
  2. additionwas added dropwise
  3. temperaturemaintaining the temperature below −40° C
  4. additionwas added dropwise
  5. filtrationbefore being filtered in vacuo
  6. dissolutionThe solid was then dissolved in 5N HCl (12 ml)
  7. extractionthe resulting orange solution extracted with ethyl acetate (10 ml)
  8. customresulted in precipitation
  9. filtrationThe solid was filtered
  10. customdried in vacuo at 50° C. overnight

出典と根拠

ORDレコード
ord-a8115c07969840e4816a657bb1e7c9bf
出典データセット
uspto-grants-2001_08
特許番号
US06281357B1

関連ノート

読み込み中…