Butyryl chloride → HCID 68971160, compound

HRID 540859Notes

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][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:9][CH:8]=[C:7]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:6]=2.[C:30](Cl)(=O)[CH2:31][CH2:32][CH3:33]>>[CH2:23]([O:22][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][S:18]([CH3:21])(=[O:19])=[O:20])[C:30]([CH2:31][CH2:32][CH3:33])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Reactant 2

HCID 8855Butyryl chloride

HCID 68900564HCID 68900564, compound

Product 1

HCID 68971160HCID 68971160, compoundYield 69.3%

Procedure

The method described in Part D of Example 45 was used to treat N-[4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]methanesulfonamide (15.1 g, 36.5 mmol) with butyryl chloride (4.77 mL, 46.2 mmol). The crude product was purified by column chromatography on silica gel (eluting with 96:4 chloroform:methanol containing ammonium hydroxide) to provide 11.8 g of N-[4-(7-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide as a tan solid.

Workup

customThe crude product was purified by column chromatography on silica gel (eluting with 96:4 chloroform:methanol containing ammonium hydroxide)

Sources & evidence

ORD record: ord-da52799fdf444da6b8c52da23e6c9cb1
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871782B2

Reaction notes

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