Hydrochloric Acid → HCID 23508141, compound

HRID 2187543Notes

Reaction equation

HRID 2187543 reaction equation
C[N:2]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[N:8]=[CH:7][C:6]([NH:14][C:15](=[O:28])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=3)=[CH:5][C:4]=2[CH2:3]1.[ClH:29]>C(OCC)C>[ClH:29].[CH3:12][C:10]1([CH3:13])[C:9]2[N:8]=[CH:7][C:6]([NH:14][C:15](=[O:28])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=3)=[CH:5][C:4]=2[CH2:3][NH:2][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9908559HCID 9908559, compound

Product 1

HCID 23508141HCID 23508141, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

N-(5,6,7,8-Tetrahydro-6,8,8-trimethyl[1,6]naphthyridin-3-yl)-4-methoxy-3-trifluoromethylbenzamide (172 mg; 0.44 mmol) was suspended in 1,2-dichloromethane (30 ml) and the mixture treated with 1-chloroethyl chlioroformate (62.5 mg: 47 ml; 0.44 mmol). The mixture was heated at reflux and more chlioroformate added until little or no starting material remained. At this point. the volatiles were removed under reduced pressure and the residue dissolved in methanol (30 ml) and heated at reflux for 15 min. The volatiles were removed under reduced pressure and the residue treated with a mixture of 0.88 aqueous ammonia/methanol/dichloromethane (0.5: 4.5:95) and the resulting, beige solid was collected by filtration. The free base (123 mg; 0.32 mmol) was dissolved in methanol (min. vol) and treated with IM hydrogen chloride in diethyl ether (0.32 ml: 0.32 mmol) and the mixture diluted with diethyl ether to turbidity and refrigerated. The title compound was obtained as white powder (130 mg: 71%).

Workup

  1. additionthe mixture treated with 1-chloroethyl chlioroformate (62.5 mg: 47 ml; 0.44 mmol)
  2. temperatureThe mixture was heated
  3. temperatureat reflux
  4. additionmore chlioroformate added until little or no starting material
  5. customthe volatiles were removed under reduced pressure
  6. dissolutionthe residue dissolved in methanol (30 ml)
  7. temperatureheated
  8. temperatureat reflux for 15 min
  9. customThe volatiles were removed under reduced pressure
  10. additionthe residue treated with a mixture of 0.88 aqueous ammonia/methanol/dichloromethane (0.5: 4.5:95)
  11. filtrationthe resulting, beige solid was collected by filtration
  12. dissolutionThe free base (123 mg; 0.32 mmol) was dissolved in methanol (min. vol)

Sources & evidence

ORD record
ord-f1dd1321fac644c590f72cef71258337
Source dataset
uspto-grants-2002_06
Patent number
US06410555B1

Reaction notes

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