Piperidine → HCID 178518493, compound

HRID 624696Notes

Reaction equation

[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].N1CCCCC1.[CH:14]1([NH:17][C:18]2[N:23]3[N:24]=[CH:25][C:26]([CH:27]=O)=[C:22]3[N:21]=[C:20]([NH:29][C:30]3[CH:35]=[C:34]([F:36])[CH:33]=[C:32]([F:37])[CH:31]=3)[CH:19]=2)[CH2:16][CH2:15]1>C(O)C.O>[CH:14]1([NH:17][C:18]2[N:23]3[N:24]=[CH:25][C:26](/[CH:27]=[C:7]4/[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1]/4)=[C:22]3[N:21]=[C:20]([NH:29][C:30]3[CH:35]=[C:34]([F:36])[CH:33]=[C:32]([F:37])[CH:31]=3)[CH:19]=2)[CH2:15][CH2:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

Hydantoin (28 mg, 0.28 mmol) and piperidine (42 μL, 0.42 mmol) were added to 7-(cyclopropylamino)-5-(3,5-difluorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (52 mg, 0.16 mmol) dissolved in ethanol (1 mL). The reaction was heated at 80° C. After 12 h, the reaction was cooled to r.t., diluted with water (2 mL), and the precipitate was collected and washed with 1:1 ethanol:water (5 mL). The solid was dried in vacuo to give (Z)-5-((7-(cyclopropylamino)-5-(3,5-difluorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (18 mg, 28% over 3 steps). LCMS (M+1=440)

Workup

temperaturethe reaction was cooled to r.t.
customthe precipitate was collected
washwashed with 1:1 ethanol
customThe solid was dried in vacuo

Sources & evidence

ORD record: ord-9f66240c23ef4899955a61fc97bcc648
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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