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Ethyl Acetate → 3-{[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-(5-methylpyrazin-2-yl)benzamide

HRID 1990276
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HRID 1990276 반응식
[CH3:1][C:2]([Si:5]([CH3:29])([CH3:28])[O:6][CH2:7][C@@H:8]([O:10][C:11]1[CH:12]=[C:13]([CH:24]=[C:25]([OH:27])[CH:26]=1)[C:14]([NH:16][C:17]1[CH:22]=[N:21][C:20]([CH3:23])=[CH:19][N:18]=1)=[O:15])[CH3:9])([CH3:4])[CH3:3].[N:30]1([C:34]([C:36]2[CH:41]=[N:40][C:39](Cl)=[CH:38][N:37]=2)=[O:35])[CH2:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C>[N:30]1([C:34]([C:36]2[N:37]=[CH:38][C:39]([O:27][C:25]3[CH:24]=[C:13]([CH:12]=[C:11]([O:10][C@@H:8]([CH3:9])[CH2:7][O:6][Si:5]([C:2]([CH3:3])([CH3:4])[CH3:1])([CH3:28])[CH3:29])[CH:26]=3)[C:14]([NH:16][C:17]3[CH:22]=[N:21][C:20]([CH3:23])=[CH:19][N:18]=3)=[O:15])=[N:40][CH:41]=2)=[O:35])[CH2:33][CH2:32][CH2:31]1
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참가 물질

6

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HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 46870328(Azetidin-1-yl)(5-chloropyrazin-2-yl)methanoneHCID 53629692HCID 53629692, 화합물

생성물 1

HCID 536296913-{[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-(5-methylpyrazin-2-yl)benzamide수율 53.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
140 °C

실험 절차

A mixture of 3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-(5-methylpyrazin-2-yl)benzamide (0.12 g, 0.29 mmol), 2-(azetidin-1-ylcarbonyl)-5-chloropyrazine (57 mg, 0.29 mmol) and potassium carbonate (80 mg, 0.57 mmol) in acetonitrile (5 mL) was stirred in a microwave reactor at 140° C. for 1 hour. The mixture was reduced in vacuo and ethyl acetate (50 mL) added. The mixture was washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and reduced in vacuo to give a brown oil which was chromatographed on silica, eluting with 50 to 100% ethyl acetate in isohexane, to give the desired compound as a colourless oil (90 mg). 1H NMR δ (CDCl3): −0.03 (s, 3H), 0.00 (s, 3H), 0.81 (s, 9H), 1.26 (d, 3H), 2.32 (quin, 2H), 2.49 (s, 3H), 3.61-3.76 (m, 2H), 4.20 (t, 2H), 4.46 (sextet, 1H), 4.62 (t, 2H), 6.91 (t, 1H), 7.21 (t, 1H), 7.32 (t, 1H), 8.07 (s, 1H), 8.28 (d, 1H), 8.30 (s, 1H), 8.79 (d, 1H), 9.48 (d, 1H). m/z 579 (M+H)+

후처리

  1. additionadded
  2. washThe mixture was washed with water (50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customto give a brown oil which
  6. customwas chromatographed on silica
  7. washeluting with 50 to 100% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-b35bf34bb1ae46b59aa7f6aefc205be5
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07642259B2

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