Hydrochloric Acid → HCID 23508141, compound

HRID 1883580Notes

Reaction equation

HRID 1883580 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.[Cl:29]C(OC(Cl)C)=O.ClC([O-])=O.Cl>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5213051-Chloroethyl chloroformateHCID 9908559HCID 9908559, compoundHCID 21226386Carbonochloridate

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 chloroformate (62.5 mg; 47 ml; 0.44 mmol). The mixture was heated at reflux and more chloroformate 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. temperatureThe mixture was heated
  2. temperatureat reflux
  3. customAt this point, the volatiles were removed under reduced pressure
  4. dissolutionthe residue dissolved in methanol (30 ml)
  5. temperatureheated
  6. temperatureat reflux for 15 min
  7. customThe volatiles were removed under reduced pressure
  8. additionthe residue treated with a mixture of 0.88 aqueous ammonia/methanol/dichloromethane (0.5:4.5:95)
  9. filtrationthe resulting, beige solid was collected by filtration
  10. dissolutionThe free base (123 mg; 0.32 mmol) was dissolved in methanol (min. vol)

Sources & evidence

ORD record
ord-06452faae8a54ee6baa0d99c6dda9b91
Source dataset
uspto-grants-2004_07
Patent number
US06762192B2

Reaction notes

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