Sodium Sulfate → HCID 10114705, compound

HRID 1271692Notes

Reaction equation

HRID 1271692 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@@H:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[N:19]=3)[N:14]=[CH:13][CH:12]=2)[OH:10])[CH2:4][CH2:3]1.[N:23]1[C:32]2[NH:31][CH2:30][CH2:29][CH2:28][C:27]=2[CH:26]=[CH:25][C:24]=1[CH:33]=O.[O-]S([O-])(=O)=O.[Na+].[Na+].[BH4-].[Na+]>C(Cl)Cl.C(O)C>[CH3:22][O:21][C:18]1[N:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[C:11]2[C@@H:9]([OH:10])[CH2:8][N:5]1[CH2:6][CH2:7][CH:2]([NH:1][CH2:33][C:24]2[CH:25]=[CH:26][C:27]3[CH2:28][CH2:29][CH2:30][NH:31][C:32]=3[N:23]=2)[CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 4311764Sodium borohydrideHCID 218737255,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehydeHCID 23400257HCID 23400257, compound

Product 1

HCID 10114705HCID 10114705, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-2-(4-aminopiperidin-1-yl)-1-(6-methoxy-[1,5]naphthyridin-4-yl)ethanol (2f) (0.30 g, 1.0 mmole) in CH2Cl2 (25 mL) and dry ethanol (10 mL) at RT was added 5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carboxaldehyde (prepared according to the procedure of WO 98/08840, 0.17 g, 1.0 mmole) and granular Na2SO4 (approximately 200 mg). After 36 h, the reaction was filtered through a sintered-glass funnel and the filtrate was concentrated. The remaining residue was dissolved in dry ethanol and reacted with NaBH4 (0.04 g, 1.0 mmole). After 12 h at RT, the reaction was concentrated under vacuum and the residue was dissolved in a mixture of H2O (2 mL) and saturated aqueous NaHCO3 (10 mL). The aqueous solution was extracted with EtOAc (2×50 mL) and the combined organic phases were washed with brine then were dried over Na2SO4. Flash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) afforded the title compound (0.37 g, 83%) as a white solid:

Workup

  1. customprepared
  2. filtrationthe reaction was filtered through a sintered-glass funnel
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe remaining residue was dissolved in dry ethanol
  5. waitAfter 12 h at RT
  6. concentrationthe reaction was concentrated under vacuum
  7. dissolutionthe residue was dissolved in a mixture of H2O (2 mL) and saturated aqueous NaHCO3 (10 mL)
  8. extractionThe aqueous solution was extracted with EtOAc (2×50 mL)
  9. washthe combined organic phases were washed with brine
  10. dry with materialthen were dried over Na2SO4

Sources & evidence

ORD record
ord-36370233f60d4fdc985a07c29a0f5fde
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Reaction notes

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