1,1,1-Trimethoxybutane → HCID 68935391, compound

HRID 2362547Notes

Reaction equation

HRID 2362547 reaction equation
[CH3:1][C:2]([CH3:23])([CH2:16][C:17]1([CH3:22])[O:21][CH2:20][CH2:19][O:18]1)[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15].[C:24](OC)(OC)(OC)[CH2:25][CH2:26][CH3:27]>>[CH3:1][C:2]([CH3:23])([CH2:16][C:17]1([CH3:22])[O:21][CH2:20][CH2:19][O:18]1)[CH2:3][N:4]1[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=[C:24]1[CH2:25][CH2:26][CH3:27]

Participants

3

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 86611638HCID 86611638, compound

Product 1

HCID 68935391HCID 68935391, compoundYield 29.2%

Procedure

The general method described in Step 6 of Example 22 was used to cyclize N4-[2,2-dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)propyl]quinoline-3,4-diamine (9.1 g, 28.9 mmol) by reaction with trimethyl orthobutyrate (4.4 g, 30 mmol) to provide 1-[2,2-dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-2-propyl-1H-imidazo[4,5-c]quinoline (3.10 g) as a solid after chromatography on silica gel (elution with a solution of 7% methanol in dichloromethane that contained about 5 mL of ammonium hydroxide solution per liter of eluent).

Sources & evidence

ORD record
ord-6fc33052d08042f9b4e3501018e41349
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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