Triethylamine → HCID 118970888, compound

HRID 930499Notes

Reaction equation

HRID 930499 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][N:20]=1)[CH2:17][NH:16][CH2:15][CH2:14]2.C(N(CC)CC)C>C1COCC1>[Cl:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][N:20]=1)[CH2:17][N:16]([C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:8])[CH2:15][CH2:14]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82604Nicotinoyl chlorideHCID 713075066-Chloro-1,2,3,4-tetrahydro-2,7-naphthyridine

Product 1

HCID 118970888HCID 118970888, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of nicotinoyl chloride (0.084 g, 0.593 mmol) in anhydrous THF (1.2 mL) was treated with 6-chloro-1,2,3,4-tetrahydro-2,7-naphthyridine (0.100 g, 0.593 mmol) and triethylamine (0.12 mL, 1.19 mmol). and subsequently allowed to stir at room temperature. After 4 hours the reaction was quenched with deionized H2O (10 mL). Following dilution with EtOAc (10 mL) the reaction mixture was washed twice with brine and once with saturated Na2HCO3(aq). The combined aqueous layers were then washed once with EtOAc. The organic layers were combined, dried over anhydrous Na2SO4(s), filtered and then concentrated in vacuo. Purification over silica using a Methanol/CHCl3 gradient afforded the desired product, in 73.3% yield (0.119356 g, 0.435 mmol).

Workup

  1. customAfter 4 hours the reaction was quenched with deionized H2O (10 mL)
  2. washwas washed twice with brine and once with saturated Na2HCO3(aq)
  3. washThe combined aqueous layers were then washed once with EtOAc
  4. dry with materialdried over anhydrous Na2SO4(s)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification over silica using a Methanol/CHCl3

Sources & evidence

ORD record
ord-698a841645c34beb8355ca7ffb3e118f
Source dataset
uspto-grants-2016_03
Patent number
US09296747B1

Reaction notes

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