Thiazolidinedione → HCID 89114984, compound

HRID 1397047Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

An 8 mL round-bottomed vial was charged with tert-butyl((1-(6-formylpyrimidin-4-yl)piperidin-4-yl)methyl)carbamate (77.9 mg, 0.24 mmol, 1 equiv.), ethanol (1 mL), thiazolidine-2,4-dione (28.5 mg, 0.24 mmol, 1 equiv.) and triethylamine (68 μL, 0.48 mmol, 2 equiv.). Piperidine (1.04 mg, 23 μL of a solution of 52 μL in 0.95 mL ethanol, 0.012 mmol, 5% eq.) was added and Argon was bubbled through the solution. The reaction mixture was shaken at 85° C. for 18 h. LC-MS of the crude reaction mixture showed mostly the desired product. The solvent was evaporated. The residue was partitioned between EtOAc (10 mL) and 10% NH4Cl (5 mL). The organic layer was dried over Na2SO4. Evaporation of solvent gave the crude (Z)-tert-butyl((1-(6-((2,4-dioxothiazolidin-5-ylidene)methyl)pyrimidin-4-yl)piperidin-4-yl)methyl)carbamate (79.8 mg, 78%). LC-MS: M+1=420.

Workup

customArgon was bubbled through the solution
customLC-MS of the crude reaction mixture

Sources & evidence

ORD record: ord-e2676dce8f7544e2b3f416fbbc50d009
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901145B2

Reaction notes

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