Hydrochloric Acid → HCID 23209293, compound

HRID 1956430Notes

Reaction equation

HRID 1956430 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH3:14])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH2:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][N:24]=1)[CH3:21].C(=O)([O-])[O-].[K+].[K+].Cl>CCOCC.C1COCC1>[ClH:1].[CH2:13]([O:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:2]2[NH:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:20][CH3:21])=[N:24][CH:25]=1)[CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 30403016-Ethoxypyridin-3-amineHCID 23209292Ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate

Product 1

HCID 23209293HCID 23209293, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate (2.1 g), 2-ethoxy-5-aminopyridine (1.08 g), anhydrous potassium carbonate (2.17 g) and THF (60 ml) was stirred at ambient temperature for 48 hours. The mixture was evaporated to dryness and water added to the residue. The mixture was extracted with dichloromethane to give an oily solid. This solid was dissolved in IMS (20 ml) and the solution saturated with hydrogen chloride gas while cooling in ice. Ether was added to induce precipitation. The mixture was filtered to give ethyl 6-ethoxy-4-(2-ethoxy-5-pyridylamino)-1,5-naphthyridine-3-carboxylate hydrochloride, m.p. 187°-189° C. Borderline active (1/1) at 30 mg/kg.

Workup

  1. customThe mixture was evaporated to dryness and water
  2. additionadded to the residue
  3. extractionThe mixture was extracted with dichloromethane
  4. customto give an oily solid
  5. customprecipitation
  6. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-37114d61854944d9bfd8fa5fdd83df14
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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