1,1,1-Trimethoxybutane → HCID 86616898, compound

HRID 606120Notes

Reaction equation

HRID 606120 reaction equation
Cl.N1C=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC)(OC)(OC)CCC.[Cl:18][C:19]1[C:28]([NH2:29])=[C:27]([NH:30][CH2:31][CH2:32][C:33]2[O:37][N:36]=[C:35]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)[CH:34]=2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1>C1(C)C=CC=CC=1>[Cl:18][C:19]1[C:28]2[N:29]=[C:3]([CH2:4][CH2:5][CH3:6])[N:30]([CH2:31][CH2:32][C:33]3[O:37][N:36]=[C:35]([C:38]4[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=4)[CH:34]=3)[C:27]=2[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:20]=1

Participants

5

Reactant 3

HCID 1235121,1,1-TrimethoxybutaneHCID 10176127Pyridinium chlorideHCID 86616896HCID 86616896, compound

Product 1

HCID 86616898HCID 86616898, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, pyridine hydrochloride (1.6 g, 14 mmol), trimethyl orthobutyrate (1.62 g, 11.0 mmol), 2-chloro-N4-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}quinoline-3,4-diamine (2.10 g, 5.49 mmol), and toluene (50 mL) were combined and heated at reflux for four hours under a Dean-Stark trap. The volatiles were removed under reduced pressure. The resulting oil was dissolved in ethyl acetate, and the solution was washed sequentially with aqueous potassium carbonate, water, and brine; dried over sodium sulfate; filtered; and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 4:6 hexane:ethyl acetate) to provide 1.22 g of 4-chloro-1-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}-2-propyl-1H-imidazo[4,5-c]quinoline as a pale yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for four hours under a Dean-Stark trap
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionThe resulting oil was dissolved in ethyl acetate
  5. washthe solution was washed sequentially with aqueous potassium carbonate, water, and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationand concentrated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel (eluting with 4:6 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-db03c7b6a61d475892a6910074b6f2fa
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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