Benzoic Acid → (Z)-tert-Butyl 4-((6-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate

HRID 1626352Notes

Reaction equation

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

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of tert-butyl 4-((6-(4-formylphenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate (950 mg, 0.002298 mole), thiazolidine-2,4-dione (241 mg, 0.00206 mole) and benzoic acid (0.0364 mg, 0.000298 mole) in toluene (30 ml), piperidine (0.033 ml, 0.00344 mole) was added and reaction mixture was refluxed for 7 hours using Dean-Stark apparatus. Then reaction mixture was cooled to 30° C. and solid product was filtered, washed with ice cold toluene and dried to yield 700 mg white solid product.

Workup

customreaction mixture
temperaturewas refluxed for 7 hours
customThen reaction mixture
filtrationsolid product was filtered
washwashed with ice cold toluene
customdried

Sources & evidence

ORD record: ord-6246c129ce9c4a2b9e5f09bd22435c91
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785463B2

Reaction notes

Loading…