Piperidine → HCID 178518497, compound

HRID 624706Notes

Reaction equation

HRID 624706 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].N1CCCCC1.[CH2:14]([S:21][C:22]1[CH:27]=[C:26]([N:28]([CH:36]2[CH2:38][CH2:37]2)C(=O)OC(C)(C)C)[N:25]2[N:39]=[CH:40][C:41]([CH:42]=O)=[C:24]2[N:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C.O>[CH2:14]([S:21][C:22]1[CH:27]=[C:26]([NH:28][CH:36]2[CH2:37][CH2:38]2)[N:25]2[N:39]=[CH:40][C:41](/[CH:42]=[C:7]3/[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1]/3)=[C:24]2[N:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 86714600Tert-butyl 5-(benzylthio)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate

Product 1

HCID 178518497HCID 178518497, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Hydantoin (67 mg, 0.67 mmol) and piperidine (66 μL, 0.67 mmol) were added to tert-butyl 5-(benzylthio)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (95 mg, 0.22 mmol) dissolved in ethanol (1.1 mL). The reaction was heated at 80° C. After 15 h, the reaction was cooled to r.t., diluted with water (5 mL), and the precipitate was collected and washed with 1:1 ethanol:water (10 mL) and then ethanol (3 mL). The bright yellow solid was dried in vacuo to give (Z)-5-((5-(benzylthio)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (75 mg, 66%). LCMS (ES): >95% pure, m/z 507 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-6b13679da5fc48c9b9a9539d76fcd926
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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