Ammonia → 5-(4-Methoxyphenyl)-2-phenyloxazole-4-carboxamide

HRID 714961Notes

Reaction equation

HRID 714961 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]([OH:22])=O)=[CH:5][CH:4]=1.COC1C=CC(C2OC(C3SC=CC=3)=[N:33]C=2C(O)=O)=CC=1.O.OC1C2N=NNC=2C=CC=1.N.O1CCOCC1.N=C=N>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]([NH2:33])=[O:22])=[CH:5][CH:4]=1

Participants

9

Reactant 6

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 160435CarbodiimideHCID 201204025-(4-Methoxyphenyl)-2-phenyloxazole-4-carboxylic acidHCID 292814635-(4-Methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxylic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 595874315-(4-Methoxyphenyl)-2-phenyloxazole-4-carboxamideYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-methoxyphenyl)-2-phenyloxazole-4-carboxylic acid (prepared according to the method described for 5-(4-methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxylic acid in Example M-1, 0.032 g, 0.11 mmol) and hydroxybenzotriazole monohydrate (0.02 g, 0.13 mmol) in DCM (2 mL) and DMF (1 mL) was added 0.5M ammonia in dioxane (1 mL, 0.5 mmol), followed by PS-carbodiimide resin. The resulting mixture was stirred at room temperature overnight. The mixture was passed through a MP-CO3 resin cartridge and the solvent removed in vacuo. The residue was purified by preparative HPLC to afford 5-(4-methoxyphenyl)-2-phenyloxazole-4-carboxamide (0.008 g, 0.03 mmol, 27%) as a white solid. 1H NMR (DMSO) δ 3.85 (3H, s), 7.10 (2H, d), 7.60 (3H, m), 7.66 (1H, br. s), 7.78 (1H, br. s), 8.14 (2H, m), 8.37 (2H, d). LCMS (2) Rt: 3.16 min; m/z (ES+) 295.

Workup

  1. customthe solvent removed in vacuo
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-865a38e484584049b3a2d52f4802a249
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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