Piperidine → HCID 178518495, compound

HRID 2036930Notes

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]([NH:16][C:17]([CH:19]3[CH2:21][CH2:20]3)=[O:18])[CH:6]=2)[CH2:3][CH2:2]1.[NH:22]1[CH2:28][C:26](=[O:27])[NH:25][C:23]1=[O:24].N1CCCCC1>C(O)C>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:28]4\[NH:22][C:23](=[O:24])[NH:25][C:26]\4=[O:27])=[C:9]3[N:8]=[C:7]([NH:16][C:17]([CH:19]3[CH2:20][CH2:21]3)=[O:18])[CH:6]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To N-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl) cyclopropanecarboxamide (74 mg, 0.26 mmol) in 1.0 mL ethanol was added hydantoin (26 mg, 0.26 mmol) and piperidine (24 ul). The reaction was heated at 80° C. for two hours. The reaction mixture was cooled to room temperature, concentrated and diluted with MeOH. The product was purified by prep HPLC to yield 14 mg (20% yield) (Z)-N-(7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide. LCMS (M+1=368)

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
additiondiluted with MeOH
customThe product was purified by prep HPLC

Sources & evidence

ORD record: ord-ffa3a2f87171430eb1692058c65e0fdf
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575177B2

Reaction notes

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