Piperidine → HCID 178518514, compound

HRID 624698Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][CH2:17][CH:18]3[CH2:20][CH2:19]3)[N:13]3[N:21]=[CH:22][C:23]([CH:24]=O)=[C:12]3[N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].[NH:26]1[CH2:32][C:30](=[O:31])[NH:29][C:27]1=[O:28].N1CCCCC1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][CH2:17][CH:18]3[CH2:19][CH2:20]3)[N:13]3[N:21]=[CH:22][C:23](/[CH:24]=[C:32]4/[C:30](=[O:31])[NH:29][C:27](=[O:28])[NH:26]/4)=[C:12]3[N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To 5-(3-chloro-4-fluorophenylamino)-7-(cyclopropylmethylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (40 mg, 0.09 mmol) in 1.0 mL of ethanol was added hydantoin (9 mg, 0.09 mmol) and piperidine (8 ul). The reaction was heated at 80° C. overnight, cooled to room temperature, filtered, and washed with ethanol to yield 20 mg (31% yield) (Z)-5-((5-(3-chloro-4-fluorophenylamino)-7-(cyclopropylmethylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene) imidazolidine-2,4-dione as a yellow powder. LCMS (M+1=442)

Workup

temperaturecooled to room temperature
filtrationfiltered
washwashed with ethanol

Sources & evidence

ORD record: ord-dc7b8aa6940c4d9ab3b7be12f10b5fb9
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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