Triethylamine → HCID 59899164, compound

HRID 2227279Notes

Reaction equation

HRID 2227279 reaction equation
Cl.Cl.[CH2:3]([O:5][C:6](=[O:28])[CH2:7][C@@H:8]([C:20]1[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[CH2:9][CH2:10][CH2:11][N:12]1[C@H:16]([CH3:17])[CH2:15][C@H:14]([NH2:18])[C:13]1=[O:19])[CH3:4].C(N(CC)CC)C.[N:36]1[C:45]2[NH:44][CH2:43][CH2:42][CH2:41][C:40]=2[CH:39]=[CH:38][C:37]=1[CH:46]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[CH2:3]([O:5][C:6](=[O:28])[CH2:7][C@@H:8]([C:20]1[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[CH2:9][CH2:10][CH2:11][N:12]1[C@H:16]([CH3:17])[CH2:15][C@H:14]([NH:18][CH2:46][C:37]2[CH:38]=[CH:39][C:40]3[CH2:41][CH2:42][CH2:43][NH:44][C:45]=3[N:36]=2)[C:13]1=[O:19])[CH3:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 218737255,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehydeHCID 70159380HCID 70159380, compound

Product 1

HCID 59899164HCID 59899164, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred suspension of 4-8 (250 mg, 0.57 mmol), triethylamine (80 mL, 0.57 mmol), and 5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carboxaldehyde (for preparation, see U.S. Pat. No. 6,048,861) (93 mg, 0.57 mmol) in 1,2-dichloroethane (5 mL) was added sodium triacetoxyborohydride (182 mg, 0.86 mmol) and the resulting mixture was stirred for 1.5 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was then washed with saturated aqueous sodium chloride, dried over magnesium sulfate, then filtered. Following evaporative removal of the solvent, the residue was purified by flash column chromatography (silica gel, 95:5:0.5:0.5% ethyl acetate/ethanol/NH4OH/H2O) to give 4-9 as a colorless oil.

Workup

  1. customfor preparation
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was then washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customremoval of the solvent
  7. customthe residue was purified by flash column chromatography (silica gel, 95:5:0.5:0.5% ethyl acetate/ethanol/NH4OH/H2O)

Sources & evidence

ORD record
ord-16ce6b70f0834d56b5886c1fb8c20471
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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