Acetone → HCID 178490642、化合物

HRID 254685ノート

反応式

HRID 254685 の反応式
[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

参加物

7

反応物 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 178490643HCID 178490643、化合物

生成物 1

HCID 178490642HCID 178490642、化合物収率 86%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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 90.6 EtOH: C, 57.95; H,6.19; N, 12.24. Found: C, 57.86; H, 6.13; N, 11.85.

後処理

  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

出典と根拠

ORDレコード
ord-8d866566d171470d8ff970eeb1419b84
出典データセット
uspto-grants-2011_01
特許番号
US07875640B2

反応ノート

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