Ethylenediamine → 3-[3-(4,5-dihydro-1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one

HRID 522321Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]([CH3:15])[CH3:14])=[C:11]([N:16]3[CH2:20][CH2:19][CH:18]([N:21]4[C:25]5=[N:26][CH:27]=[CH:28][CH:29]=[C:24]5[C:23]([C:30]#[N:31])=[N:22]4)[C:17]3=[O:32])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:33](N)[CH2:34][NH2:35]>CC(O)=O.CCO>[NH:31]1[CH2:33][CH2:34][N:35]=[C:30]1[C:23]1[C:24]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[N:21]([CH:18]2[CH2:19][CH2:20][N:16]([C:11]3[CH:10]=[N:9][N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[C:12]=3[CH:13]([CH3:14])[CH3:15])[C:17]2=[O:32])[N:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-[1-[1-(4-fluorophenyl)-5-isopropyl-pyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-b]pyridine-3-carbonitrile (0.082 g, 0.19 mmol) in ethane-1,2-diamine (1 mL), HOAc (0.1 mL) and EtOH (2.5 mL) was stirred at 100° C. for 1 hr. The mixture was then cooled to room temperature, quenched with saturated aqueous NaHCO3 (50 mL) and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-[3-(4,5-dihydro-1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.085 g, 94%).

Workup

temperatureThe mixture was then cooled to room temperature
customquenched with saturated aqueous NaHCO3 (50 mL)
extractionextracted with EtOAc (100 mL)
customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-38f561c15de24ce6b72704f33c33ebb8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328116B2

Reaction notes

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