Dimethyl Sulfoxide → HCID 22240510, compound

HRID 2422981Notes

Reaction equation

HRID 2422981 reaction equation
C([CH:3]1[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=2)[C:6](=[O:16])[C:5]2[N:17]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[N:18]=[C:19]([C:20]([NH2:22])=[O:21])[C:4]1=2)C.C(OC([N:41]1[CH2:46][CH2:45][NH:44][C:43](=[O:47])[CH2:42]1)=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CS(C)=O>CCOC(C)=O.O.[Cu]I>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([N:17]2[C:5]3[C:6](=[O:16])[N:7]([C:9]4[CH:10]=[CH:11][C:12]([N:44]5[CH2:45][CH2:46][NH:41][CH2:42][C:43]5=[O:47])=[CH:13][CH:14]=4)[CH2:8][CH2:3][C:4]=3[C:19]([C:20]([NH2:22])=[O:21])=[N:18]2)=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 67242817HCID 67242817, compound

Product 1

HCID 22240510HCID 22240510, compoundYield 43.4%

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

Part A. To ethyl-6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxamide (0.52 g, 1.0 mmol), 4-benzyloxycarbonylpiperazin-2-one (0.32 g, 1.4 mmol), and K2CO3 (0.22 g, 1.6 mmol) was added DMSO (5 mL). The mixture was degassed with N2. CuI (38 mg, 0.2 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 by chromatography on silica gel using 5% MeOH/CH2Cl2 afforded 0.2 g (33%) of a foam; Mass Spec (M+H)+ 624.6.

Workup

  1. customThe mixture was degassed with N2
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. customPurification by chromatography on silica gel using 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-c1f2ab0390784f9e8adf16339d97c30b
Source dataset
uspto-grants-2011_06
Patent number
US07960411B2

Reaction notes

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