Ethyl Acetate → HCID 68672510, compound

HRID 1927673Notes

Reaction equation

[CH3:1][C:2]([CH3:25])([CH2:23][CH3:24])[CH2:3][C:4](=O)[CH2:5][NH:6][C:7](=O)[CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:11]=1.C([O-])(=O)C.[NH4+:30].C(OCC)(=O)C.[OH-].[NH4+]>C(O)(=O)C.O>[CH3:1][C:2]([CH3:25])([CH2:23][CH3:24])[CH2:3][C:4]1[NH:30][C:7]([CH2:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:11]=2)=[N:6][CH:5]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To N-(4,4-dimethyl-2-oxohexyl)-3-(3-pyridin-2-yl-[1,2,4]oxadiazol-5-yl)propionamide (413 mg, 1.2 mmol) in acetic acid (3 mL) was added ammonium acetate (924 mg, 12 mmol), and the mixture was heated at 180° C. for 20 minutes in a microwave reactor (maximum 150 W). The reaction mixture was poured into ethyl acetate and water, and pH of the aqueous layer was adjusted to 9 with concentrated ammonium hydroxide. The organic layer was separated and concentrated to give a residue. The residue was purified by flash column chromatography (silica gel, eluting with 0-15% 9:1 methanol/ammonium hydroxide mixture in methylene chloride) to afford the title compound, which was converted to the HCl salt with 1M HCl in diethyl ether. 1H NMR (500 MHz, CD3OD) δ 8.83-8.85 (m, 1H), 8.32-8.35 (m, 2H), 7.84-7.89 (m, 1H), 7.22 (s, 1H), 3.59-3.61 (m, 4H), 2.21 (s, 2H), 1.26 (q, J=7.7 Hz, 2H), 0.85 (m, 9H); LC-MS: m/e 326 (M+H).

Workup

customThe organic layer was separated
concentrationconcentrated
customto give a residue
customThe residue was purified by flash column chromatography (silica gel, eluting with 0-15% 9:1 methanol/ammonium hydroxide mixture in methylene chloride)

Sources & evidence

ORD record: ord-e01112b1736d42029a420ee8ff005ee3
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183275B2

Reaction notes

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