Hydrochloric Acid → HCID 86633069, compound

HRID 1094215Notes

Reaction equation

HRID 1094215 reaction equation
CS(C)=O.[CH:5]1([NH:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:32])[C:17]([CH2:27][CH2:28][CH2:29][CH2:30][OH:31])=[CH:18][N:19]3[CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:14][C:13]=2[F:33])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C.Cl>O>[CH:5]1([NH:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:32])[C:17]([CH2:27][CH2:28][CH2:29][CH:30]=[O:31])=[CH:18][N:19]3[CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:14][C:13]=2[F:33])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 66637055HCID 66637055, compound

Product 1

HCID 86633069HCID 86633069, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 4 ml DMSO solution of 310 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-(4-hydroxybutyl)quinolin-4(1H)-one was added 0.7 ml of triethylamine and 620 mg of a sulfur trioxide pyridine complex, followed by stirring at room temperature for 24 hours. By adding 1 M hydrochloric acid and water, the insoluble materials were collected by filtration to obtain 290 mg of 4-[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]butanal.

Workup

  1. filtrationthe insoluble materials were collected by filtration

Sources & evidence

ORD record
ord-6561efd72a5643bca2b4c04a70c48015
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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