Isopropyl iodide → HCID 58958570、化合物

HRID 915594ノート

反応式

HRID 915594 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:8]([CH3:10])[CH3:9].[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([NH:22][C:23]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:25][CH:24]=2)=[C:17]([CH:21]=1)[C:18]([OH:20])=[O:19]>CN(C=O)C>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([NH:22][C:23]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:25][CH:24]=2)=[C:17]([CH:21]=1)[C:18]([O:20][CH:8]([CH3:10])[CH3:9])=[O:19]

参加物

5

反応物 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 589586195-methoxy-2-[(1-phenyl-1H-pyrazol-5-yl)amino]benzoic acid

生成物 1

HCID 58958570HCID 58958570、化合物収率 59%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Cesium carbonate (105 mg, 0.19 mmol) and 2-iodopropane (18 mg, 0.11 mmol) were added to a solution of the intermediate 5-methoxy-2-[(1-phenyl-1H-pyrazol-5-yl)amino] benzoic acid (30 mg, 0.10 mmol) in DMF (4 mL). The mixture was stirred at rt for 16 h. The reaction was quenched with water (5 mL) and then extracted with dichloromethane (3×5 mL). The combined organic layers were washed with water (5 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. HPLC purification of the residue (YMC propack C18 column, 150×20 mm ID, 30%-80% acetonitrile in water gradient) afforded the desired product as a white solid (20 mg, 59%). 1H NMR (300 MHz, DMSO-d6) δ 9.07 (s, 1H), 7.65 (d, 1H), 6.96-7.56 (m, 9H), 6.29 (dd, 1H), 5.06 (q, 1H), 3.69 (s, 3H), 1.24 (d, 6H); ES-MS m/z 352.1 (MH+); HPLC RT (min) 3.53.

後処理

  1. customThe reaction was quenched with water (5 mL)
  2. extractionextracted with dichloromethane (3×5 mL)
  3. washThe combined organic layers were washed with water (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customHPLC purification of the residue (YMC propack C18 column, 150×20 mm ID, 30%-80% acetonitrile in water gradient)

出典と根拠

ORDレコード
ord-fe82ba2049a54c6dbf039174a4f840cf
出典データセット
uspto-grants-2007_09
特許番号
US07265144B2

反応ノート

読み込み中…