1,1,1-Trimethoxybutane → HCID 69177470, compound

HRID 1373949Notes

Reaction equation

HRID 1373949 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:9][CH:8]=[C:7]([Br:21])[CH:6]=2.[C:22](OC)(OC)(OC)[CH2:23][CH2:24][CH3:25]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.Cl.N1C=CC=CC=1>[Br:21][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[C:22]([CH2:23][CH2:24][CH3:25])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

Participants

6

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 21075822HCID 21075822, compound

Product 1

HCID 69177470HCID 69177470, compoundYield 70.7%

Reagents, catalysts & solvents 3

HCID 10176127Pyridinium chlorideCatalystHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

A solution of tert-butyl N′-(3-amino-7-bromoquinolin-4-yl)hydrazinecarboxylate (37.1 g, 105 mmol) in 315 mL of toluene was treated with trimethyl orthobutyrate (16.7 mL, 105 mmol) and pyridine hydrochloride (0.12 g, 1.05 mmol). The reaction mixture was heated to reflux under an atmosphere of nitrogen. After 4 h, the reaction mixture was cooled to ambient temperature and concentrated under reduced pressure to give a brown oil. The oil was dissolved in 300 mL of CHCl3. The solution was washed with 5% Na2CO3 (100 mL), water (100 mL) and brine (100 mL). The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to yield a brown foam. The foam was purified by chromatography (SiO2, 100:0 gradient to 95:5 CHCl3:MeOH) to yield 30.1 g of tert-butyl (7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)carbamate as a light brown solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under an atmosphere of nitrogen
  3. concentrationconcentrated under reduced pressure
  4. customto give a brown oil
  5. washThe solution was washed with 5% Na2CO3 (100 mL), water (100 mL) and brine (100 mL)
  6. dry with materialThe organic portion was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield a brown foam
  10. customThe foam was purified by chromatography (SiO2, 100:0 gradient to 95:5 CHCl3:MeOH)

Sources & evidence

ORD record
ord-ca7d5ee468584e84a6eb3d8255d410d4
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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