1-Bromo-2-methylbutane → 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-isopropylpyridin-2-yl)-N-(2-methylbutyl)benzenesulfonamide

HRID 594172

반응식

HRID 594172 반응식
[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][N:20]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:28])[O:4][N:3]=1.C(N=C(N(C)C)N(C)C)(C)(C)C.Br[CH2:42][CH:43]([CH3:46])[CH2:44][CH3:45]>C(#N)C>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([N:18]([C:19]3[CH:24]=[CH:23][C:22]([CH:25]([CH3:26])[CH3:27])=[CH:21][N:20]=3)[CH2:42][CH:43]([CH3:46])[CH2:44][CH3:45])(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[C:5]([CH3:28])[O:4][N:3]=1

참가 물질

5

반응물 3

HCID 252541-Bromo-2-methylbutaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898760154-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

생성물 1

HCID 721949364-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-isopropylpyridin-2-yl)-N-(2-methylbutyl)benzenesulfonamide수율 4.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
20 °C

실험 절차

To a solution of 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (156 mg, 0.389 mmol) in acetonitrile (4 mL) stirred in air at 20° C., was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (133 mg, 0.777 mmol). The reaction mixture was stirred at 20° C. for 1 hour, then 1-bromo-2-methylbutane (117 mg, 0.777 mmol) was added. The reaction then heated by microwaves to 150° C., for 30 minutes. After cooling the solvent was removed in vacuo and diluted with ethyl acetate. The organic phase was washed with water (5 mL), then dried using a hydrophobic frit. The solvent was removed in vacuo to give the crude product as an orange oil. Purification of the crude was attempted using flash silica (Si) chromatography (0-25% ethylacetate-cyclohexane gradient) followed by mass directed autoprep (ammonium carbonate modifier), however impurities still remained. A final purification using a silica (Si) cartridge (eluting with a gradient of 0-25% ethyl acetate-cyclohexane) provided a small amount of clean product (8.5 mg) as a colourless oil. LCMS (2 min, High pH) Rt 1.48 mins, m/z (ES+) 472 (M+H).

후처리

  1. customThe reaction
  2. temperaturethen heated by microwaves to 150° C., for 30 minutes
  3. temperatureAfter cooling the solvent
  4. customwas removed in vacuo
  5. additiondiluted with ethyl acetate
  6. washThe organic phase was washed with water (5 mL)
  7. customdried
  8. customThe solvent was removed in vacuo
  9. customto give the crude product as an orange oil
  10. customPurification of the crude
  11. customA final purification
  12. washeluting with a gradient of 0-25% ethyl acetate-cyclohexane)

출처 및 근거

ORD 기록
ord-5f62b9dab19b43c6b62e1a6e2d9ad25b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242972B2

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