Dimethyl Sulfoxide → HCID 68939045, compound

HRID 2362501Notes

Reaction equation

[CH2:1]([C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH:21]([OH:23])[CH3:22])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4].CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C>>[CH2:1]([C:5]1[N:6]([CH2:18][CH2:19][CH2:20][C:21](=[O:23])[CH3:22])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 8471Triethylamine

HCID 65578Oxalyl chloride

HCID 57455400HCID 57455400, compound

Product 1

HCID 68939045HCID 68939045, compoundYield 61%

Procedure

The general method described in Step 8 of Example 1 was used to oxidize 5-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-ol (3.54 g, 11.4 mmol) with DMSO (1.33 g, 17.1 mmol), oxalyl chloride (1.59 g, 12.5 mmol), and triethylamine (3.45 g, 34.1 mmol) to provide 5-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one (2.15 g) as a dark solid.

Sources & evidence

ORD record: ord-f59bb02dbbef4164b5c433c3a6c62f1c
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691837B2

Reaction notes

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