1,1,1-Trimethoxybutane → HCID 68933444, compound

HRID 521320Notes

Reaction equation

HRID 521320 reaction equation
[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[CH2:5][CH2:6][NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[NH2:18])[CH3:2].[C:22](OC)(OC)(OC)[CH2:23][CH2:24][CH3:25]>>[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[CH2:5][CH2:6][N:7]1[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=[C:22]1[CH2:23][CH2:24][CH3:25])[CH3:2]

Participants

3

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 86052493HCID 86052493, compound

Product 1

HCID 68933444HCID 68933444, compoundYield 91.3%

Procedure

The general method described in Step 3 of Example 15 was used to cyclize N4-(3,3-diethoxypropyl)quinoline-3,4-diamine (20.7 g, 71.5 mmol) by reaction with trimethyl orthobutyrate (13.2 g, 89.4 mmol) to provide 1-(3,3-diethoxypropyl)-2-propyl-1H-imidazo[4,5-c]quinoline (22.3 g) as a dark oil that was used directly in the next step without further purification.

Sources & evidence

ORD record
ord-c5f3aed61d0c4398a45cedaf8798b196
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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