Piperidine → HCID 178481606, compound

HRID 2037018Notes

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]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[CH:6]=2)[CH2:3][CH2:2]1.[CH3:25][N:26]1[C:30](=[O:31])[CH2:29][NH:28][C:27]1=[O:32].N1CCCCC1>CCO.O>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:29]4\[NH:28][C:27](=[O:32])[N:26]([CH3:25])[C:30]\4=[O:31])=[C:9]3[N:8]=[C:7]([NH:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[CH:6]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

4-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile (51 mg, 0.16 mmol) was suspended in EtOH (1.6 mL). 3-methylimidazolidine-2,4-dione (28 mg, 0.24 mmol) and piperidine (24 μL, 0.24 mmol) were added and the reaction was heated to 80° C. After 15 h, the solution was diluted with H2O (2 mL) and filtered. The filter cake was washed with 50% H2O/50% EtOH (3 mL) and then dried in vacuo (˜1 mmHg) to furnish (Z)-4-(7-(cyclopropylamino)-3-((1-methyl-2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile (45 mg, 68%) as a bright yellow solid. LCMS (ES): >90% pure, tm/z 415 [M+1]+.

Workup

filtrationfiltered
washThe filter cake was washed with 50% H2O/50% EtOH (3 mL)
customdried in vacuo (˜1 mmHg)

Sources & evidence

ORD record: ord-1c3bf94d896b44e6b0d966a8f7068211
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575177B2

Reaction notes

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