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 447893Notes

Reaction equation

HRID 447893 reaction equation
[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]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 17027464Gkt-136901

Product 1

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

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5ec31d4216d24e85bd6fe553ad608844
Source dataset
uspto-grants-2013_07
Patent number
US08481562B2

Reaction notes

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