Ceric ammonium nitrate → 4-(4-chlorophenyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]-pyrazol-6(1H)-one

HRID 873928Notes

Reaction equation

HRID 873928 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH3:16])=[N:13][N:12]([C:17]4[C:18]([O:23][CH3:24])=[N:19][CH:20]=[CH:21][CH:22]=4)[C:11]=3[C:10](=[O:25])[N:9]2CC2C=CC(OC)=CC=2)=[CH:4][CH:3]=1.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>CC#N.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH3:16])=[N:13][N:12]([C:17]4[C:18]([O:23][CH3:24])=[N:19][CH:20]=[CH:21][CH:22]=4)[C:11]=3[C:10](=[O:25])[NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 1177027704-(4-chlorophenyl)-5-(4-methoxybenzyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Product 1

HCID 1177026734-(4-chlorophenyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]-pyrazol-6(1H)-oneYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-(4-chlorophenyl)-5-(4-methoxybenzyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 71.3) (2.8 g, 5.90 mmol) in CH3CN (80 mL) and H2O (20 mL) was added CAN (9.70 g, 17.69 mmol) and the reaction mixture was stirred at RT for 16 hr. The reaction mixture was quenched with brine and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 1-2.5%). The residue was triturated in CH2Cl2 to afford the title product (1.06 g, 2.93 mmol, 50% yield) as white solid. tR: 4.36 min (HPLC 1); tR: 0.98 min (LC-MS 2); ESI-MS: 355 [M+H]+ (LC-MS 2); Rf=0.39 (CH2Cl2/MeOH 9:1).

Workup

  1. customThe reaction mixture was quenched with brine
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 1-2.5%)
  7. customThe residue was triturated in CH2Cl2

Sources & evidence

ORD record
ord-658d2b1a09b44126bcad015175229598
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…