P-Anisidine → HCID 58842857、化合物

HRID 16958

反応式

HRID 16958 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C1N=CN([C:15](N2C=NC=C2)=[O:16])C=1.[CH2:22]([O:24][C:25](=[O:44])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N:34]2[C:38]([NH2:39])=[CH:37][C:36]([C:40]([CH3:43])([CH3:42])[CH3:41])=[N:35]2)[CH:29]=1)[CH3:23]>CN(C=O)C>[CH2:22]([O:24][C:25](=[O:44])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N:34]2[C:38]([NH:39][C:15]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[O:16])=[CH:37][C:36]([C:40]([CH3:43])([CH3:42])[CH3:41])=[N:35]2)[CH:29]=1)[CH3:23]

参加物

5

反応物 3

HCID 7732P-AnisidineHCID 682631,1'-CarbonyldiimidazoleHCID 58842892ethyl 3-(3-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl)propanoate

生成物 1

HCID 58842857HCID 58842857、化合物収率 45.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A mixture of 4-methoxy-phenylamine (123 mg, 1.0 mmol) and CDI (165 mg, 1.0 mmol) in DMF (2 mL) was stirred at RT for 30 min, and was then added a solution of Example Z (315 mg, 1.0 mmol) in DMF (2 mL). The resulting mixture was stirred at RT overnight then quenched with of water (50 mL). The reaction mixture was extracted with ethyl acetate (3×50 mL) and the combined organic extracts were washed with brine, dried (NaSO4), filtered, concentrated under reduced presume to yield a residue which was purified by flash chromatography to afford 3-(3-{3-t-butyl-5-[3-(4-methoxy-phenyl)-ureido]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester (210 mg, 45%). 1H-NMR (CD3OD): 7.46 (t, J=7.6 Hz, 1H), 7.38 (s, 1H), 7.34 (d, J=7.6 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 6.84 (d, J=8.4 Hz, 2H), 6.38 (s, 1H), 4.09 (q, J=7.2 Hz, 2H), 3.75 (s, 3H), 3.00 (t, J=7.6 Hz, 2H), 2.68 (t, J=7.6 Hz, 2H), 1.33 (s, 9H), 1.20 (t, J=7.6 Hz, 3H); MS (ESI) m/z: 465 (M+H+).

後処理

  1. stirringThe resulting mixture was stirred at RT overnight
  2. customthen quenched with of water (50 mL)
  3. extractionThe reaction mixture was extracted with ethyl acetate (3×50 mL)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (NaSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced presume
  8. customto yield a residue which
  9. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-5fff6ba8bad6477891b99d6173706b19
出典データセット
uspto-grants-2010_06
特許番号
US07737283B2

関連ノート

読み込み中…