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 447893노트

반응식

HRID 447893 반응식
[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]

참가 물질

4

반응물 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 17027464Gkt-136901

생성물 1

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

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온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ec31d4216d24e85bd6fe553ad608844
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481562B2

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