Hydrochloric Acid → HCID 21109092, compound

HRID 1766091Notes

Reaction equation

HRID 1766091 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=1)=[N:5][C:6]([S:17][CH3:18])=[N:7]2.O.O.Cl[Sn]Cl.CCO.Cl>O1CCOCC1>[NH2:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1)=[N:5][C:6]([S:17][CH3:18])=[N:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 21109098HCID 21109098, compound

Product 1

HCID 21109092HCID 21109092, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of ethyl 5-amino-2-methylthio-4-(3-nitro-phenyl)-quinazoline-6-carboxylate (example 27e, 1.54 g) and SnCl2.2H2O (4.52 g) in 1,4-dioxane (35 ml) were added EtOH (35 ml) and concentrated aqueous HCl (690 l). The reaction mixture was stirred at 90° C. for 5 h. After cooling to room temperature and concentration under reduced pressure the residue was suspended in EtOAc (35 ml). The mixture was brought to pH 10 by the addition of 2 M NaOH and THF and brine were added. The resulting mixture was stirred for 40 min, after which time the organic layer was seperated, dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel using hept/EtOAc=9/1 to 3/2 (v/v) as eluent.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationconcentration under reduced pressure the residue
  3. additionThe mixture was brought to pH 10 by the addition of 2 M NaOH and THF and brine
  4. additionwere added
  5. stirringThe resulting mixture was stirred for 40 min
  6. customafter which time the organic layer was seperated
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe title compound was purified by chromatography on silica gel using hept/EtOAc=9/1 to 3/2 (v/v) as eluent

Sources & evidence

ORD record
ord-bad9d5c0e6ff441c9b86e7420a9e32fb
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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