Hydrochloric Acid → (racemic) N-(5-cyano-4-isopropoxypyridin-2-yl)-7-formyl-6-(tetrahydrofuran-3-yl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

HRID 1778117Notes

Reaction equation

HRID 1778117 reaction equation
Cl.[C:2]([C:4]1[C:5]([O:33][CH:34]([CH3:36])[CH3:35])=[CH:6][C:7]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([CH:28]4[CH2:32][CH2:31][O:30][CH2:29]4)=[C:20]([CH:23](OC)[O:24]C)[N:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[N:8][CH:9]=1)#[N:3].C([O-])(O)=O.[Na+]>C1COCC1.O>[C:2]([C:4]1[C:5]([O:33][CH:34]([CH3:36])[CH3:35])=[CH:6][C:7]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([CH:28]4[CH2:32][CH2:31][O:30][CH2:29]4)=[C:20]([CH:23]=[O:24])[N:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[N:8][CH:9]=1)#[N:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 118036843(racemic) N-(5-cyano-4-isopropoxypyridin-2-yl)-7-(dimethoxymethyl)-6-(tetrahydrofuran-3-yl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide2×

Product 1

HCID 118036512(racemic) N-(5-cyano-4-isopropoxypyridin-2-yl)-7-formyl-6-(tetrahydrofuran-3-yl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Concentrated HCl (0.26 ml) was added to a solution of (racemic) N-(5-cyano-4-isopropoxypyridin-2-yl)-7-(dimethoxymethyl)-6-(tetrahydrofuran-3-yl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 336, 157 mg, 0.314 mmol) in THF (1.2 ml) and H2O (0.4 ml) at room temperature. After stirring for 5 h at room temperature, sat. aq. NaHCO3 was added and the mixture extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The residue was triturated with Et2O to give the title compound as a white solid.

Workup

  1. extractionthe mixture extracted with EtOAc (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-a3a51c6e80cb442ca27895dac6c4e484
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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