1,1,1-Trimethoxybutane → HCID 69507145, compound

HRID 1623131Notes

Reaction equation

HRID 1623131 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][CH2:14][CH2:15][CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(O[CH:25](OCC)[CH2:26][CH2:27][CH2:28]NC1C2C(=CC=CC=2)N=C(N)C=1)C.C(OC)(OC)(OC)CCC.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:13]([CH2:14][CH2:15][CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19])[C:25]([CH2:26][CH2:27][CH3:28])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Participants

5

Reactant 4

HCID 1235121,1,1-Trimethoxybutane2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 69507133HCID 69507133, compoundHCID 86052855HCID 86052855, compound

Product 1

HCID 69507145HCID 69507145, compound

Procedure

A modification of the general method of Part B of Example 6 was followed using 7-bromo-N4-(4,4-dimethoxybutyl)quinoline-3,4 diamine (59.3 g, 167.39 mmol) in lieu of N4-(4,4-diethoxybutyl)quinoline-2,4 diamine. The reaction was incomplete after running overnight. Trimethyl orthobutyrate (5 mL) was added to the reaction mixture and heated to reflux for an additional 2 hours, upon which an additional amount of trimethyl orthobutyrate (5 mL) and pyridinium tosylate (5 mL) were added. After 2 hours of heating to reflux, the mixture was concentrated under reduced pressure, diluted in dichloromethane (300 mL) and methanol (45 mL), washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, and the mixture was concentrated under reduced pressure to afford 57.0 g of 7-bromo-1-(4,4-dimethoxybutyl)-2-propyl-1H-imidazo[4,5-c]quinoline as a brown solid.

Workup

  1. temperatureheated
  2. additionwere added
  3. temperatureAfter 2 hours of heating
  4. temperatureto reflux
  5. concentrationthe mixture was concentrated under reduced pressure
  6. additiondiluted in dichloromethane (300 mL)
  7. washmethanol (45 mL), washed with saturated aqueous sodium bicarbonate solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b8c256aa5fdc4ceaa865dafd00a8e23c
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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