Acetic Anhydride → 1-acetyl-2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione

HRID 447893ノート

反応式

HRID 447893 の反応式
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:32](=[O:33])[C:18]2=[C:19]([CH3:31])[N:20]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[C:21](=[O:23])[CH:22]=[C:17]2[NH:16]1.C([O-])(=O)C.[Na+]>>[C:1]([N:16]1[C:17]2[C:18](=[C:19]([CH3:31])[N:20]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[C:21](=[O:23])[CH:22]=2)[C:32](=[O:33])[N:15]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[Cl:8])(=[O:3])[CH3:2]

参加物

4

反応物 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 17027464Gkt-136901

生成物 1

HCID 498375711-acetyl-2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione収率 82%

反応条件

温度
40 °C

実験手順

10.0 ml of acetic anhydride was added to a mixture of 2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione (Compound of Formula (Ia) (0.250 g, 0.682 mmol, 1 equiv.) and sodium acetate (0.056 g, 0.682 mmol, 1 equiv). The resulting mixture was heated at 40° C. for 1 h and then concentrated in vacuo. The resulting residue was dissolved in EtOAc and washed with water. The organic phase was dried over Na2SO4 and concentrated in vacuo until dryness to afford 0.228 g of the desired compound 1-acetyl-2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione as a white solid (82% yield). Rf (EtOAc) 0.34; 1H NMR (500 MHz, CDCl3) 2.08 (s, 3H), 2.95 (s, 3H), 5.47 (s, 2H), 7.04 (s, 1H), 7.21 (m, 1H), 7.37-7.32 (m, 4H), 7.56 (m, 1H), 7.67 (td, J 7.6, 1.9 Hz, 1H), 8.51 (m, 1H); MS (ESI+): 409.2; MS (ESI−): 407.7.

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in EtOAc
  3. washwashed with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo until dryness

出典と根拠

ORDレコード
ord-5ec31d4216d24e85bd6fe553ad608844
出典データセット
uspto-grants-2013_07
特許番号
US08481562B2

反応ノート

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