Hydrochloric Acid → N-(5-cyano-4-ethylpyridin-2-yl)-6,7-diformyl-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

HRID 1778099Notes

Reaction equation

HRID 1778099 reaction equation
Cl.[C:2]([C:4]1[C:5]([CH2:30][CH3:31])=[CH:6][C:7]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([CH:28]=[O:29])=[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]([CH2:30][CH3:31])=[CH:6][C:7]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([CH:28]=[O:29])=[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 Acid2×HCID 516892Sodium BicarbonateHCID 118036273N-(5-cyano-4-ethyl pyridin-2-yl)-7-(dimethoxymethyl)-6-formyl-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide2×

Product 1

HCID 118036925N-(5-cyano-4-ethylpyridin-2-yl)-6,7-diformyl-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Concentrated hydrochloric acid (0.10 ml) was added to a solution of N-(5-cyano-4-ethylpyridin-2-yl)-7-(dimethoxymethyl)-6-formyl-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 110, 50 mg, 0.122 mmol) in THF (4 ml) and water (0.5 ml) at room temperature. After stirring for 3 h additional concentrated hydrochloric acid (0.10 ml) was added and the reaction mixture stirred for a further 48 h at room temperature. Saturated aqueous NaHCO3 was added, the mixture extracted with DCM (2×), the organic layers dried over Na2SO4 and evaporated to give the title compound as a beige solid. (UPLC-MS 6) tR 1.13 min, ESI-MS 364.2, [M+H]+.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with DCM (2×)
  3. dry with materialthe organic layers dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-eb21bed386df4e3cbc062851d068b6a5
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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