3-Aminopyridine → Tert-butyl 3-(pyridin-3-ylcarbamoyl)piperazine-1-carboxylate

HRID 70231Notes

Reaction equation

HRID 70231 reaction equation
O=[C:2]1[CH:6]2[CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][N:5]2C(=O)[O:3]1.[NH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1>C1COCC1.O>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([NH:19][C:2]([CH:6]2[NH:5][CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7]2)=[O:3])[CH:21]=1

Participants

5

Reactant 2

HCID 100093-AminopyridineHCID 18722816tert-butyl 1,3-dioxotetrahydro-1H-oxazolo[3,4-a]pyrazine-7(3H)-carboxylate

Product 1

HCID 59671553Tert-butyl 3-(pyridin-3-ylcarbamoyl)piperazine-1-carboxylateYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 1,3-dioxotetrahydro-1H-oxazolo[3,4-a]pyrazine-7(3H)-carboxylate (1.50 g, 5.85 mmol) and 3-aminopyridine (1.10 g, 11.7 mmol) were heated to reflux in THF (20 mL). After 4 h, the reaction mixture was cooled to rt, diluted with H2O (50 mL), and was extracted with EtOAc (3×75 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was purified by column chromatography (0 to 8% MeOH in CH2Cl2 with 0.5% NH4OH gradient), yielding 0.740 g (44%) of the title compound. LC-MS: RT=4.14 min, [M+H]+=307.1.

Workup

  1. extractionwas extracted with EtOAc (3×75 mL)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe material was purified by column chromatography (0 to 8% MeOH in CH2Cl2 with 0.5% NH4OH gradient)

Sources & evidence

ORD record
ord-b885abff01704823b2aec33fa555fbda
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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