Iodoethane → HCID 58902035、化合物

HRID 1992410ノート

反応式

HRID 1992410 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[NH:16][C:17](=[O:25])[N:18]3[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[C:19]=23)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:27][CH3:28]>CCO.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([O:25][CH2:27][CH3:28])[N:18]3[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[C:19]=23)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 6340IodoethaneHCID 136038645HCID 136038645、化合物

生成物 1

HCID 58902035HCID 58902035、化合物

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 702Ethanol溶媒

実験手順

A solution of 1-(3-benzyloxy-phenyl)-8-chloro-2H-imidazo[1,5-a]pyrazin-3-one (50.0 mg, 0.14 mmol) and silver carbonate (85 mg, 0.31 mmol) in anhydrous EtOH (1 mL) was charged with iodoethane (0.012 mL, 0.15 mmol) and stirred at rt for 48 h. The reaction mixture was partitioned between DCM and H2O and separated. The aqueous layer was washed with DCM (3×) and the combined organic layers were washed with brine (1×), dried over Na2SO4, filtered and concentrated in vacuo and the crude material was purified by chromatography on silica gel [eluting with 2% EtOAc in DCM], to yield the desired product as a yellow oil/gum; 1H NMR (CDCl3, 400 MHz) δ 1.51 (t, J=7.2 Hz, 3H), 4.68 (q, J=7.2 Hz, 2H), 5.13 (s, 2H), 7.00-7.05 (m, 1H), 7.13 (d, J=5.2 Hz, 1H), 7.27-7.48 (m, 9H); MS (ES+) m/z=380.07 (100) [MH+], HPLC: tR=4.04 min (MicromassZQ, polar—5 min).

後処理

  1. customThe reaction mixture was partitioned between DCM and H2O
  2. customseparated
  3. washThe aqueous layer was washed with DCM (3×)
  4. washthe combined organic layers were washed with brine (1×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe crude material was purified by chromatography on silica gel [eluting with 2% EtOAc in DCM]

出典と根拠

ORDレコード
ord-eb35503074bb4c80acb8dca09ef57b48
出典データセット
uspto-grants-2010_01
特許番号
US07648987B2

反応ノート

読み込み中…