Hydrochloric Acid → N-(4,5-dicyanopyridin-2-yl)-7-formyl-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

HRID 1778078Notes

Reaction equation

HRID 1778078 reaction equation
[C:1]([C:3]1[C:8]([C:9]#[N:10])=[CH:7][N:6]=[C:5]([NH:11][C:12]([N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH:24](OC)[O:25]C)[N:22]=3)[CH2:17][CH2:16][CH2:15]2)=[O:13])[CH:4]=1)#[N:2].O.Cl>C1COCC1.CCOC(C)=O>[C:1]([C:3]1[C:8]([C:9]#[N:10])=[CH:7][N:6]=[C:5]([NH:11][C:12]([N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH:24]=[O:25])[N:22]=3)[CH2:17][CH2:16][CH2:15]2)=[O:13])[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 118036695N-(4,5-dicyanopyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide2×

Product 1

HCID 118037038N-(4,5-dicyanopyridin-2-yl)-7-formyl-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4,5-dicyanopyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 2F, 15 mg, 0.040 mmol) was dissolved in THF (0.6 ml) and water (0.6 ml) and treated at room temperature with conc. HCl (0.10 ml). The reaction mixture was stirred at room temperature for 1.5 h, diluted in EtOAc and washed with sat. aq. NaHCO3 (2×) and brine. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was triturated with MeOH, the solid was filtered and dried overnight at 40° C. under vacuum to obtain the title compound as a white solid.

Workup

  1. washwashed with sat. aq. NaHCO3 (2×) and brine
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated with MeOH
  6. filtrationthe solid was filtered
  7. customdried overnight at 40° C. under vacuum

Sources & evidence

ORD record
ord-e5f1ea04b98a46bc926e5a26efdb46a4
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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