Diisopropylethylamine → HCID 86655010, compound

HRID 2066860Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][C:4](=[N:7][O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:3][CH2:2]1.[F:21][C:22]1[CH:27]=[C:26](F)[C:25]([F:29])=[CH:24][C:23]=1[C:30](=[O:32])[CH3:31].CCN(C(C)C)C(C)C>CS(C)=O>[CH:18]([O:17][C:15]([N:12]1[CH2:11][CH2:10][CH:9]([O:8][N:7]=[C:4]2[CH2:3][CH2:2][N:1]([C:26]3[CH:27]=[C:22]([F:21])[C:23]([C:30](=[O:32])[CH3:31])=[CH:24][C:25]=3[F:29])[CH2:6][CH2:5]2)[CH2:14][CH2:13]1)=[O:16])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 130 °C

Procedure

Compound 2d (0.22 g, 0.78 mmol), 1-(2,4,5-trifluoro-phenyl)-ethanone (0.22 mL), DIEA (0.22 mL, 1.33 mmol), and DMSO (2 mL) were combined and heated at 130° C. for 20 h. The mixture was cooled to room temperature and purified by flash chromatography (eluent: 10 to 40% EtOAc+0.1% triethylamine in hexane) to afford 211 mg (62% yield) of 4-[1-(4-acetyl-2,5-difluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester 50a: LC-MS 438.0 (MH+).

Workup

temperatureThe mixture was cooled to room temperature
custompurified by flash chromatography (eluent: 10 to 40% EtOAc+0.1% triethylamine in hexane)

Sources & evidence

ORD record: ord-bf8ff5a933834cb4b396fc7fd7a02e56
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293729B2

Reaction notes

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