Aminopyrazine → HCID 9967123, compound

HRID 1827125Notes

Reaction equation

HRID 1827125 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1)=O.[NH2:19][C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH2:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][CH:3]([CH2:1][NH:19][C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)[CH2:4][CH2:5]1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 78747AminopyrazineHCID 2776272Benzyl 4-formylpiperidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 9967123HCID 9967123, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Benzyl 4-formyl-1-piperidinecarboxylate (P. E. Maligres, Tetrahedron, 53(32):10983–10992(1997)) (100 mg, 0.40 mmol) and aminopyrazine (46 mg, 0.48 mmol) were dissolved in toluene under N2 and was heated to reflux under Dean Stark conditions for 18 h. The volatiles were removed in vacuo and the residue taken up in ethanol and treated with solid NaBH4 (76 mg, 2.00 mmol) in small portions. The reaction aged at 20° C. for 1 h then was quenched with 2N HCl. The reaction was basified with 1M NaOH and was extracted with ethyl acetate (2×). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified by reverse phase HPLC to give the title compound as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under Dean Stark conditions for 18 h
  3. customThe volatiles were removed in vacuo
  4. customthen was quenched with 2N HCl
  5. extractionwas extracted with ethyl acetate (2×)
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-8348d93734c44d92a8b846801f900bb8
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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