Triethylamine → HCID 86596852, compound

HRID 1373958Notes

Reaction equation

HRID 1373958 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]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:6]=2.C(N(CC)CC)C.[CH2:36]([O:38][CH2:39][C:40](Cl)=O)[CH3:37]>ClCCCl.C(O)CCC.C(Cl)(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:22]([O: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]([CH3:20])([CH3:19])[CH3:18])[C:37]([CH2:36][O:38][CH2:39][CH3:40])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 21075821tert-butyl N'-(3-amino-7-benzyloxyquinolin-4-yl)hydrazinecarboxylate

Product 1

HCID 86596852HCID 86596852, compoundYield 41.3%

Reagents, catalysts & solvents 4

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 111,2-DichloroethaneSolventHCID 2631-ButanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
135 °C

Procedure

A suspension of tert-butyl N′-(3-amino-7-benzyloxyquinolin-4-yl)hydrazinecarboxylate (29.6 g, 77.8 mmol) in 250 mL of 1,2-dichloroethane was placed under an atmosphere of nitrogen. The mixture was treated with triethylamine (30.9 mL, 233 mmol). The mixture was then treated dropwise with ethoxyacetyl chloride (10.5 g, 85.6 mmol). After 2 h, the reaction was concentrated under reduced pressure to give a brown oil. The oil was dissolved in 200 mL of 1-butanol and treated with pyridinium p-toluenesulfonate (0.25 g, 1.0 mmol). The mixture was heated to 135° C. under an atmosphere of nitrogen. After 20 h, the reaction mixture was cooled to ambient temperature and concentrated under reduced pressure to give a brown oil. The oil was dissolved in 250 mL of CHCl3 and washed with saturated NaHCO3 solution (75 mL), water (75 mL) and brine (75 mL). The organic portion was then dried over Na2SO4, filtered and concentrated under reduced pressure to give an orange/brown oil. The oil was purified by chromatography (SiO2, 9:1 CHCl3:MeOH) to yield 14.4 g of tert-butyl (7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)carbamate as an orange/brown foam.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. customto give a brown oil
  3. waitAfter 20 h
  4. temperaturethe reaction mixture was cooled to ambient temperature
  5. concentrationconcentrated under reduced pressure
  6. customto give a brown oil
  7. washwashed with saturated NaHCO3 solution (75 mL), water (75 mL) and brine (75 mL)
  8. dry with materialThe organic portion was then dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto give an orange/brown oil
  12. customThe oil was purified by chromatography (SiO2, 9:1 CHCl3:MeOH)

Sources & evidence

ORD record
ord-b042900229714910b5347afa40dd545a
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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