Acetone → HCID 178490642, 화합물

HRID 538827노트

반응식

HRID 538827 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:8](=[N:21][C:22]#[N:23])/[N:9]=[C:10]2\[S:11][CH:12]=[C:13]([CH3:20])[N:14]\2[CH2:15][CH:16]2[CH2:19][CH2:18][CH2:17]2)[CH:7]=1.C([N-]C(C)C)(C)C.[Li+].[CH3:34][C:35]([CH3:37])=[O:36].[Cl-].[NH4+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:8](=[N:21][C:22]#[N:23])/[N:9]=[C:10]2\[S:11][C:12]([C:35]([OH:36])([CH3:37])[CH3:34])=[C:13]([CH3:20])[N:14]\2[CH2:15][CH:16]2[CH2:19][CH2:18][CH2:17]2)[CH:7]=1

참가 물질

7

반응물 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 178490643HCID 178490643, 화합물

생성물 1

HCID 178490642HCID 178490642, 화합물수율 86%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Example 110D (101 mg, 0.269 mmol) in anhydrous tetrahydrofuran (4 mL) at −78° C. was added lithium diisopropylamide (2 M, 0.404 mL). After 5 min acetone (46.9 mg, 0.808 mmol) was added and the reaction was stirred for 0.5 hrs. Saturated ammonium chloride solution (2 mL) was added to quench the reaction at this temperature. The reaction mixture was diluted with water and extracted with ethyl acetate (3×10 mL). The organic layers were combined, washed with brine, dried with sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-20% ethyl acetate in hexane) to afford the title compound (65 mg, 86%). 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.67 (s, 6H) 1.81-1.94 (m, 4H) 2.00-2.08 (m, 2H) 2.50 (s, 3H) 2.68-2.81 (m, 1H) 3.91 (s, 3H) 4.30 (d, J=7.12 Hz, 2H) 6.91-6.96 (m, 1H) 7.33-7.38 (m, 2H); MS (DCI/NH3) m/z 433 (M+H)+. Anal. calcd C21H25ClN4O2S.0.6 EtOH: C, 57.95; H, 6.19; N, 12.24. Found: C, 57.86; H, 6.13; N, 11.85.

후처리

  1. customto quench
  2. customthe reaction at this temperature
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. washwashed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-491155f54cf0498ca329648b6766b49e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865753B2

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