Piperidine → HCID 178518485, compound

HRID 2036931Notes

Reaction equation

HRID 2036931 reaction equation
[CH:1]1([NH:6][C:7]2[CH:12]=[C:11]([NH:13][CH:14]3[CH2:16][CH2:15]3)[N:10]3[N:17]=[CH:18][C:19]([CH:20]=O)=[C:9]3[N:8]=2)[CH2:5][CH2:4][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:6][C:7]2[CH:12]=[C:11]([NH:13][CH:14]3[CH2:16][CH2:15]3)[N:10]3[N:17]=[CH:18][C:19](/[CH:20]=[C:28]4/[C:26](=[O:27])[NH:25][C:23](=[O:24])[NH:22]/4)=[C:9]3[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 58314303HCID 58314303, compound

Product 1

HCID 178518485HCID 178518485, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

5-(Cyclopentylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (1.0 eq, 20 mg, 0.070 mmol) was mixed in a vial with hydantoin (2.8 eq, 20 mg, 0.20 mmol) in Ethanol (0.3 ml). Piperidine (2.9 eq, 20 ul, 0.202 mmol) was added and the mixture was stirred at 90° C. for 3 hours. The mixture was cooled down, the precipitate was filtered, washed with ethanol and dried. (Z)-5-((5-(cyclopentylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione was isolated as a solid (25 mg, 100%). LCMS (ES):>95% pure, m/z 368 [M+H]+.

Workup

  1. temperatureThe mixture was cooled down
  2. filtrationthe precipitate was filtered
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-1e84395b858f41f5a521afb22b1725b1
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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