Potassium Carbonate → HCID 69516704, compound

HRID 971162Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:18])[NH:15][CH2:16][CH2:17][C:12]=3[C:11]([C:19]#[N:20])=[N:10]2)=[CH:5][CH:4]=1.I[C:22]1[CH:27]=[CH:26][C:25]([C:28]([CH3:37])([CH3:36])[CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][C:31]2=[O:35])=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>[Cu]I>[CH3:37][C:28]([C:25]1[CH:24]=[CH:23][C:22]([N:15]2[CH2:16][CH2:17][C:12]3[C:11]([C:19]#[N:20])=[N:10][N:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[C:13]=3[C:14]2=[O:18])=[CH:27][CH:26]=1)([CH3:36])[CH2:29][N:30]1[CH2:34][CH2:33][CH2:32][C:31]1=[O:35]

Participants

Conditions

Temperature: 130 °C

Procedure

To 1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carbonitrile (0.149 g, 0.55 mmol), 1-[2-(4-iodo-phenyl)-2-methyl-propyl]-pyrrolidin-2-one (0.19 g, 0.55 mmol), and K2CO3 (0.23 g, 1.7 mmol) was added degassed DMSO (4 mL) followed by CuI (21 mg, 0.11 mmol). The mixture was heated to 130° C. for 5 h. The reaction was cooled, partitioned between ethyl acetate and water, extracted with ethyl acetate, and dried (MgSO4). Chromatography on silica gel using 0–5% MeOH in CH2Cl2 followed by further purification by HPLC afforded the title

Workup

customdegassed DMSO (4 mL)
temperatureThe reaction was cooled
custompartitioned between ethyl acetate and water
extractionextracted with ethyl acetate
dry with materialdried (MgSO4)
customChromatography on silica gel using 0–5% MeOH in CH2Cl2 followed by further purification by HPLC
customafforded the title

Sources & evidence

ORD record: ord-6d42646a5c05489285b90764cdd6f0d2
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312214B2

Reaction notes

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