Isopropyl methanesulfonate → HCID 178490704, 화합물

HRID 76268

반응식

HRID 76268 반응식
[C:1]([N:5]1[CH:9]=[C:8]([CH2:10][OH:11])/[C:7](=[N:12]/[C:13](=[O:23])[C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])/[S:6]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CS(O[CH:31]([CH3:33])[CH3:32])(=O)=O>O1CCOCC1>[C:1]([N:5]1[CH:9]=[C:8]([CH2:10][O:11][CH:31]([CH3:33])[CH3:32])/[C:7](=[N:12]/[C:13](=[O:23])[C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])/[S:6]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 13551Isopropyl methanesulfonateHCID 24758Sodium hydrideHCID 178490701HCID 178490701, 화합물

생성물 1

HCID 178490704HCID 178490704, 화합물수율 9.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

The product from Example 28A (50 mg, 0.14 mmol) in dioxane (5 mL) was treated with NaH (60%) (7 mg, 0.17 mmol) stirred at rt for 10 min and treated with isopropyl methanesulfonate (78 mg, 0.56 mmol). The reaction was heated at 85° C. for 12 hrs, quenched with H2O, the mixture was extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 5.2 mg (9%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.22 (d, J=6.14 Hz, 6 H) 1.81 (s, 9 H) 3.75-3.83 (m, 1 H) 4.12 (s, 3 H) 4.92 (s, 2 H) 7.10 (d, J=9.21 Hz, 1 H) 7.63 (dd, J=9.21, 2.76 Hz, 1 H) 8.18 (d, J=2.45 Hz, 1 H) 9.28 (s, 1 H); MS (DCI/NH4+) m/z 397 (M+H)+.

후처리

  1. temperatureThe reaction was heated at 85° C. for 12 hrs
  2. customquenched with H2O
  3. extractionthe mixture was extracted with EtOAc (2×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-f76b4618b6294c59beb6babd42585b5d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835475B2

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