Piperidine → HCID 178433767, compound

HRID 2037032Notes

Reaction equation

HRID 2037032 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[N:8]1([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:25]=[C:24]([NH:26][CH:27]4[CH2:29][CH2:28]4)[N:23]4[N:30]=[C:31]([CH3:35])[C:32]([CH:33]=O)=[C:22]4[N:21]=3)=[CH:15][CH:14]=2)[CH:12]=[CH:11][CH:10]=[N:9]1.N1CCCCC1>C(O)C.O>[N:8]1([C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20]3[CH:25]=[C:24]([NH:26][CH:27]4[CH2:29][CH2:28]4)[N:23]4[N:30]=[C:31]([CH3:35])[C:32]([CH:33]=[C:7]5[NH:1][C:2](=[O:3])[NH:4][C:5]5=[O:6])=[C:22]4[N:21]=3)=[CH:17][CH:18]=2)[CH:12]=[CH:11][CH:10]=[N:9]1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 583140345-(4-(1H-pyrazol-1-yl)phenylamino)-7-(cyclopropylamino)-2-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Product 1

HCID 178433767HCID 178433767, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Hydantoin (3 mg, 0.03 mmol) and 5-(4-(1H-pyrazol-1-yl)phenylamino)-7-(cyclopropylamino)-2-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde (12 mg, 0.03 mmol) were dissolved in ethanol (0.4 mL) along with piperidine (3 uL, 0.03 mmol). The reaction was heated at 80° C. in the microwave for 2 hours. The reaction was then cooled to r.t., diluted with water, and the precipitate was collected and washed with water, 1:1 ethanol:water, then ethanol. The yellow solid was dried in vacuo to give 5-((5-(4-(1H-pyrazol-1-yl)phenylamino)-7-(cyclopropylamino)-2-methylpyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (9.5 mg, 65% yield). LCMS (M+1=456)

Workup

  1. temperatureThe reaction was then cooled to r.t.
  2. customthe precipitate was collected
  3. washwashed with water, 1:1 ethanol
  4. customThe yellow solid was dried in vacuo

Sources & evidence

ORD record
ord-f1b447844e2b4e6fbbe29b8881efb743
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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