Piperidine → HCID 178510024, compound

HRID 624797Notes

Reaction equation

HRID 624797 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.[NH:25]1[CH2:31][C:29](=[O:30])[NH:28][C:26]1=[O:27].N1CCCCC1>CCO>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:31]4\[NH:25][C:26](=[O:27])[NH:28][C:29]\4=[O:30])=[C:9]3[N:8]=[C:7]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=3)[CH:6]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 866546564-(7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile

Product 1

HCID 178510024HCID 178510024, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

4-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile (75 mg, 0.24 mmol) was suspended in EtOH (2.4 mL). Hydantoin (36 mg, 0.35 mmol) and piperidine (36 μL, 0.35 mmol) were added and the reaction was heated to 80° C. After 15 h, the solution was filtered while warm and the filter cake was washed with warm EtOH (3 mL) to give (Z)-4-(7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile (76 mg, 80%) as a bright yellow solid. LCMS (ES): >90% pure, m/z 401 [M+1]+.

Workup

  1. filtrationthe solution was filtered
  2. temperaturewhile warm
  3. washthe filter cake was washed with warm EtOH (3 mL)

Sources & evidence

ORD record
ord-83b9341355ce49d3a2853417b570f125
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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