1,1,1-Trimethoxybutane → HCID 57447018, compound

HRID 2366606Notes

Reaction equation

HRID 2366606 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:23](OC)(OC)(OC)[CH2:24][CH2:25][CH3:26]>C1(C)C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:24]([C:23]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH2:25][CH3:26]

Participants

5

Reactant 2

HCID 1235121,1,1-Trimethoxybutane2×HCID 57447017HCID 57447017, compound

Product 1

HCID 57447018HCID 57447018, compound

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)Catalyst2×HCID 1140TolueneSolvent

Procedure

A solution ethyl 6-[(3-aminoquinolin-4-yl)amino]hexanoate (25.15 g, 83.4 mmol, prepared in Part A of Example 8) in toluene (400 mL) was treated with trimethyl orthobutyrate (15.4 mL, 96.2 mmol) and pyridinium p-toluenesulfonate (0.20 g, 0.80 mmol) according to, a modification of the method described in Part D of Example 6. The reaction was not complete after five hours and was allowed to cool to ambient temperature overnight. Additional pyridinium p-toluenesulfonate (0.20 g, 0.80 mmol) and trimethyl orthobutyrate (2.0 mL, 12 mmol) were added. The reaction was heated at reflux for two hours and then subjected to the work-up procedure to provide 25.0 g of ethyl 6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanoate.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for two hours

Sources & evidence

ORD record
ord-9a9e4d480e384f0a970bfd174e35ba2e
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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