Phosphorus oxychloride → HCID 46898366、化合物

HRID 602810ノート

反応式

HRID 602810 の反応式
[C:1]1([S:7]([C:10]([CH:20]2[CH2:32][C:23]3[NH:24][C:25]4[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][C:30]=4[C:22]=3[CH2:21]2)([F:19])[C:11]2[O:15][N:14]=[C:13]([C:16]([NH2:18])=O)[N:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[C:1]1([S:7]([C:10]([CH:20]2[CH2:32][C:23]3[NH:24][C:25]4[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][C:30]=4[C:22]=3[CH2:21]2)([F:19])[C:11]2[O:15][N:14]=[C:13]([C:16]#[N:18])[N:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychloride2 回HCID 11340480HCID 11340480、化合物

生成物 1

HCID 46898366HCID 46898366、化合物収率 12.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of 170 mg (0.35 mmol) of (RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid amide in 2 mL acetonitrile at RT was added 0.5 mL phosphorous oxychloride. The dark brown solution was stirred for 1 hour and then the temperature was raised to 50° C. and stirred overnight. After cooling down to RT, 0.5 mL phosphorous oxychloride were added. The reaction mixture was stirred for 2 hours under reflux condition. The solvent was partially evaporated and the resulting oil was dissolved with EtOAc and washed with saturated NaHCO3 solution. The organic phase was dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel (EtOAc/heptane 1:1) yielded 20 mg (12%) (RS, SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carbonitrile as a light red solid, MS: 457 (MH+).

後処理

  1. stirringstirred overnight
  2. temperatureAfter cooling down to RT
  3. stirringThe reaction mixture was stirred for 2 hours
  4. temperatureunder reflux condition
  5. customThe solvent was partially evaporated
  6. dissolutionthe resulting oil was dissolved with EtOAc
  7. washwashed with saturated NaHCO3 solution
  8. dry with materialThe organic phase was dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-4432f10497b24bfb8a9f579e73517c20
出典データセット
uspto-grants-2011_03
特許番号
US07906546B2

反応ノート

読み込み中…