Triethylamine → HCID 59899161, compound

HRID 2227285Notes

Reaction equation

HRID 2227285 reaction equation
Cl.Cl.[CH2:3]([O:5][C:6](=[O:27])[CH2:7][C@@H:8]([C:20]1[CH:21]=[N:22][C:23]([CH3:26])=[N: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:35]1[C:44]2[NH:43][CH2:42][CH2:41][CH2:40][C:39]=2[CH:38]=[CH:37][C:36]=1[CH:45]=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:27])[CH2:7][C@@H:8]([C:20]1[CH:25]=[N:24][C:23]([CH3:26])=[N:22][CH:21]=1)[CH2:9][CH2:10][CH2:11][N:12]1[C@H:16]([CH3:17])[CH2:15][C@H:14]([NH:18][CH2:45][C:36]2[CH:37]=[CH:38][C:39]3[CH2:40][CH2:41][CH2:42][NH:43][C:44]=3[N:35]=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 70159387HCID 70159387, compound

Product 1

HCID 59899161HCID 59899161, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred suspension of 5-5 (170 mg, 0.44 mmol), triethylamine (61 mL, 0.44 mmol), and 5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carbaldehyde (72 mg, 0.44 mmol) in 1,2-dichloroethane (4 mL) was added sodium triacetoxyborohydride (112 mg, 0.53 mmol) and the resulting mixture was stirred for 1.5 hours. The reaction mixture 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, and 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 5-6 as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was then washed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customremoval of the solvent
  6. 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-5d7ed18fbc9f423694bfab5d28435eb7
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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