Benzoic Acid → HCID 72804131, compound

HRID 273489Notes

Reaction equation

[C:1]([C:4]1[CH:33]=[CH:32][C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH3:23])[C:13]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=2)=[C:6]([Cl:34])[CH:5]=1)(=O)[CH3:2].[S:35]1[CH2:39][C:38](=[O:40])[NH:37][C:36]1=[O:41].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[Cl:34][C:6]1[CH:5]=[C:4]([C:1](=[C:39]2[S:35][C:36](=[O:41])[NH:37][C:38]2=[O:40])[CH3:2])[CH:33]=[CH:32][C:7]=1[O:8][CH2:9][CH2:10][O:11][C:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH3:23])[C:13]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of compound 3-[2-(4-Acetyl-2-chloro-phenoxy)-ethoxy]-2-(3,4-difluoro-phenyl)-1-methyl-1H-quinolin-4-one (97 g, 200 mmol), thiazolidine-2,4-dione (141 g, 1200 mmol), benzoic acid (44 g, 361 mmol) and piperidine (35 g, 411.7 mmol) were taken a single neck round bottomed flask, to this toluene (1000 mL) was added. The round-bottomed flask 20 was fitted with dean stark apparatus, which was connected to a reflux condenser. The reaction mixture was heated to reflux for 48 hours under a nitrogen atmosphere. The reaction mixture was cooled to 25° C. and was allowed to pass through a silica gel column. The product was eluted by using 0.3-0.9% MeOH/CHCl3 to afford the title compound, 37 g (32%) as off white solid.

Workup

customThe round-bottomed flask 20 was fitted with dean stark apparatus, which
customwas connected to a reflux condenser
temperatureThe reaction mixture was heated
temperatureto reflux for 48 hours under a nitrogen atmosphere
washThe product was eluted

Sources & evidence

ORD record: ord-ed01ef056c204d6782754f2980e8ce3f
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456288B2

Reaction notes

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