Dimethyl Sulfoxide → HCID 46235653, compound

HRID 892323Notes

Reaction equation

HRID 892323 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11]3[C:14]([S:25]([CH3:28])(=[O:27])=[O:26])=[N:15][N:16]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[C:10]=3[C:9]2=[O:29])=[CH:4][CH:3]=1.C(OC([N:40]1[CH2:45][CH2:44][NH:43][C:42](=[O:46])[CH2:41]1)=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CS(C)=O>CCOC(C)=O.O.[Cu]I>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([N:16]2[C:10]3[C:9](=[O:29])[N:8]([C:5]4[CH:6]=[CH:7][C:2]([N:43]5[CH2:44][CH2:45][NH:40][CH2:41][C:42]5=[O:46])=[CH:3][CH:4]=4)[CH2:13][CH2:12][C:11]=3[C:14]([S:25]([CH3:28])(=[O:27])=[O:26])=[N:15]2)=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 22250092HCID 22250092, compound

Product 1

HCID 46235653HCID 46235653, compoundYield 35.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To 6-(4-iodophenyl)-1-(4-methoxyphenyl)-3-(methylsulfonyl)-1,4,5,6-tetrahydro-7H-pyrazolo (3,4-c)pyridin-7-one (0.55 g, 1.0 mmol), 4-benzyloxycarbonylpiperazin-2-one (0.35 g, 1.4 mmol), and K2CO3 (0.23 g, 1.6 mmol) was added DMSO (5 mL). The mixture was degassed with N2. CuI (39 mg, 0.21 mmol) was added and the reaction was heated to 130° C. for 18 h. The reaction was diluted with EtOAc and water, extracted with EtOAc, and dried (MgSO4). Purification of the intermediate by chromatography on silica gel using 5% MeOH/CH2Cl2 was followed by deprotection in refluxing TFA. Purification by HPLC and freeze-drying afforded 175 mg (27%) of a white solid; High Resolution Mass Spec (M+H)+ for C24H26N6O5S 496.1650.

Workup

  1. customThe mixture was degassed with N2
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. customPurification of the intermediate by chromatography on silica gel using 5% MeOH/CH2Cl2
  5. temperaturein refluxing TFA
  6. customPurification by HPLC
  7. customfreeze-drying

Sources & evidence

ORD record
ord-9c9a12d290c94ffd915880911390b138
Source dataset
uspto-grants-2006_02
Patent number
US07005435B2

Reaction notes

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