Phosphorus oxychloride → HCID 46898366, 화합물

HRID 602810노트

반응식

HRID 602810 반응식
[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

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychloride2회HCID 11340480HCID 11340480, 화합물

생성물 1

HCID 46898366HCID 46898366, 화합물수율 12.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-4432f10497b24bfb8a9f579e73517c20
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906546B2

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