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Cyclopentanol → 12-Chloro-9-cyclopentyloxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513769
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HRID 513769 반응식
[H-].[Na+].[CH:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[Cl:9][C:10]1[CH:11]=[C:12]2[C:21](=[C:22]3[C:27]=1[CH:26]=[CH:25][CH:24]=[N:23]3)[NH:20][S:19](=[O:29])(=[O:28])[C:18]1[C:13]2=[CH:14][C:15](F)=[CH:16][CH:17]=1.OS([O-])(=O)=O.[K+]>CN1C(=O)CCC1>[Cl:9][C:10]1[CH:11]=[C:12]2[C:21](=[C:22]3[C:27]=1[CH:26]=[CH:25][CH:24]=[N:23]3)[NH:20][S:19](=[O:29])(=[O:28])[C:18]1[C:13]2=[CH:14][C:15]([O:8][CH:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)=[CH:16][CH:17]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 6818318212-Chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

생성물 1

HCID 6016476112-Chloro-9-cyclopentyloxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide수율 20%

시약·촉매·용매 1

HCID 13387
N-methyl-2-pyrrolidone
용매

실험 절차

NaH (60% in mineral oil; 53 mg, 1.34 mmol) was added to a solution of cyclopentanol (115 mg, 1.34 mmol) in NMP (3 ml) and the mixture was stirred at room temperature for 15 min. 12-chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 503 (150 mg, 0.44 mmol) was added and the mixture was heated at 180 C in a microwave for 2 h. After cooling, the mixture was poured into ice cold water and neutralized using sat aq. KHSO4 solution. The resulting precipitate was collected by filtration and dried. The crude solid was purified by column chromatography with n-hexane/DCM (30:70) as the eluent to give the title compound (23 mg, 20%).

후처리

  1. temperaturethe mixture was heated at 180 C in a microwave for 2 h
  2. temperatureAfter cooling
  3. additionthe mixture was poured into ice cold water
  4. filtrationThe resulting precipitate was collected by filtration
  5. customdried
  6. customThe crude solid was purified by column chromatography with n-hexane/DCM (30:70) as the eluent

출처 및 근거

ORD 기록
ord-c4d73bf1d803409f93ac5ccb34dbfd6c
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102688B2

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