1,1,1-Trimethoxybutane → HCID 22320428, compound

HRID 1178276Notes

Reaction equation

HRID 1178276 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][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].[C:19](OC)(OC)(OC)[CH2:20][CH2:21][CH3:22]>Cl.N1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][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:19]1[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 86588277HCID 86588277, compound

Product 1

HCID 22320428HCID 22320428, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 10176127Pyridinium chlorideCatalyst

Procedure

Using the general method of Example 1 Part D, N4-(5-chloropentyl)quinolin-3,4-diamine (˜20.4 mmol) was cyclized using trimethyl orthobutyrate (3.6 g, 24.5 mmol) in the presence of pyridine hydrochloride (˜0.1 g). The crude product was purified by column chromatography (silica gel eluting with 95/5 dichloromethane/methanol) to provide 3.9 g of 1-(5-chloropentyl)-2-propyl-1H-imidazo[4,5-c]quinoline as a light green solid.

Workup

  1. customThe crude product was purified by column chromatography (silica gel eluting with 95/5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-a1b3305825784777923966bc17ebf1cd
Source dataset
uspto-grants-2007_10
Patent number
US07276515B2

Reaction notes

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