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Thionyl Chloride → 2-(4-{4-Methyl-5-[2-(trifluoromethyl)phenyl]-4h-1,2,4-triazol-3-yl}bicyclo[2.2.2]oct-1-yl)-5-(3,3,3-trifluoro-1-methylpropyl)-1,3,4-oxadiazole

HRID 2079837
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HRID 2079837 반응식
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])=[N:5][N:4]=[C:3]1[C:17]12[CH2:24][CH2:23][C:20]([C:25]([NH:27][NH:28][C:29](=[O:37])[CH:30]([CH3:36])[CH2:31][C:32]([F:35])([F:34])[F:33])=O)([CH2:21][CH2:22]1)[CH2:19][CH2:18]2.S(Cl)(Cl)=O>C1(C)C=CC=CC=1.CC#N>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:14])([F:16])[F:15])=[N:5][N:4]=[C:3]1[C:17]12[CH2:24][CH2:23][C:20]([C:25]3[O:37][C:29]([CH:30]([CH3:36])[CH2:31][C:32]([F:34])([F:35])[F:33])=[N:28][N:27]=3)([CH2:21][CH2:22]1)[CH2:19][CH2:18]2
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참가 물질

5

반응물 2

HCID 24386Thionyl ChlorideHCID 575723784-{-4-Methyl-5-[2-(trifluoromethyl)phenyl]-4h-1,2,4-triazol-3-yl}-n'-(4,4,4-trifluoro-2-methylbutanoyl)bicyclo[2.2.2]octane-1-carbohydrazide

생성물 1

HCID 575723742-(4-{4-Methyl-5-[2-(trifluoromethyl)phenyl]-4h-1,2,4-triazol-3-yl}bicyclo[2.2.2]oct-1-yl)-5-(3,3,3-trifluoro-1-methylpropyl)-1,3,4-oxadiazole

시약·촉매·용매 2

HCID 1140Toluene용매
HCID 6342
Acetonitrile
용매

반응 조건

온도
85 °C

실험 절차

To 13-B in toluene (3 mL) was added thionyl chloride (2 mL) and, fitted with a reflux condenser, the solution was heated to 85° C. under a nitrogen atmosphere. After 1 hour the solvent was stripped off in vacuo. The residue was dissolved in CH3CN (4 ml) and product was purified by Masslynx reverse phase chromatography eluting with a 10-90% CH3CN (0.1% TFA)/water (0.1% TFA) gradient. Solvent was removed in vacuo and the product free based from methylene chloride and saturated aqueous sodium bicarbonate. The organic layer was washed with brine and dried over MgSO4. The solvent was removed and the product lyopholyzed from CH3CN and water to afford 13-C as a white solid. MS (ESI+)=514.22 (M+1); 1H NMR (500 MHz, CDCl3): δ 7.85-7.83 (m, 1 H), 7.72-7.68 (m, 2 H), 7.52 (t, 1 H), 3.48 (s, 3 H), 3.46 (m, 1 H), 2.86-2.74 (m, 1 H), 2.51-2.39 (m, 1 H), 2.28 (m, 6 H), 2.14 (m, 6 H), 1.50 (d, 3 H) ppm.

후처리

  1. customfitted with a reflux condenser
  2. customproduct was purified by Masslynx reverse phase chromatography
  3. washeluting with a 10-90% CH3CN (0.1% TFA)/water (0.1% TFA) gradient
  4. customSolvent was removed in vacuo
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed

출처 및 근거

ORD 기록
ord-c9fd1cbf89004fd79765ea7977e82f70
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932280B2

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