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Potassium Cyanide → (s)-[3-(4-Fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-6-yl]-acetonitrile

HRID 8279
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인쇄 미리보기

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HRID 8279 반응식
[C-:1]#[N:2].[K+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[N:14][N:13]3[C@H:23]([CH2:26]OS(C)(=O)=O)[CH2:24][CH2:25][C:12]=23)=[CH:7][CH:6]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O.C(OCC)(=O)C>[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[N:14][N:13]3[C@H:23]([CH2:26][C:1]#[N:2])[CH2:24][CH2:25][C:12]=23)=[CH:7][CH:6]=1
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참가 물질

7

반응물 2

HCID 9032Potassium CyanideHCID 87799512(S)-methanesulfonic acid 3-(4-fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-ylmethyl ester

생성물 1

HCID 9902141(s)-[3-(4-Fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-6-yl]-acetonitrile

시약·촉매·용매 4

HCID 67553Tetrabutylammonium Iodide촉매
HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

A mixture of potassium cyanide (44 mg, 0.67 mmol), tetrabutylammonium iodide (catalytic), and (S)-methanesulfonic acid 3-(4-fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-ylmethyl ester (54 mg, 0.135 mmol) in N,N-dimethylformamide (0.35 mL) and water (0.13 mL) is heated at 70° C. for 4 h. The mixture is cooled, taken up in ethyl acetate (20 mL), washed with water and brine, dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (2% methanol/chloroform) to yield the title compound, 25 mg (56%).

후처리

  1. temperatureThe mixture is cooled
  2. washwashed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on SiO2 (2% methanol/chloroform)

출처 및 근거

ORD 기록
ord-5b953fa7674c4f19b380bf9e67c072b5
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07087626B2

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