Ethanol → HCID 178509730, compound

HRID 624745Notes

Reaction equation

[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=O)=[C:9]3[N:8]=[C:7]([CH2:16][C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])[CH:6]=2)[CH2:3][CH2:2]1.C(O)C.[NH:28]1[CH2:34][C:32](=[O:33])[NH:31][C:29]1=[O:30].N1CCCCC1>O>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=[C:34]4[C:32](=[O:33])[NH:31][C:29](=[O:30])[NH:28]4)=[C:9]3[N:8]=[C:7]([CH2:16][C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])[CH:6]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

To the reaction flask, 3-((7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile (28 mg, 0.09 mmol) was added to ethanol (0.5 mL) along with hydantoin (9 mg, 0.09 mmol) and piperidine (9 μL, 0.09 mmol). The reaction was heated at 80° C. for 30 minutes in the microwave then cooled to room temperature and diluted with water. The solid was collected by filtration, washed with water, 50% ethanol/water, and then 100% ethanol. The material was dried under vacuum overnight. The product, 3-((7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was recovered as a solid in 34% yield. LCMS (M+1=400)

Workup

temperaturethen cooled to room temperature
filtrationThe solid was collected by filtration
washwashed with water, 50% ethanol/water
customThe material was dried under vacuum overnight
customThe product, 3-((7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was recovered as a solid in 34% yield

Sources & evidence

ORD record: ord-fff466232d9d4363aa471d1c967b3555
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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