Isopropyl iodide → HCID 58958570, 화합물

HRID 915594

반응식

HRID 915594 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 58958570HCID 58958570, 화합물수율 59%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fe82ba2049a54c6dbf039174a4f840cf
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265144B2

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