HCID 87369755, compound → 5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorobenzonitrile

HRID 245353Notes

Reaction equation

[Si:1]([O:18][CH2:19][C:20]1[C:21]([N:31]2[CH2:36][C@H:35]([CH3:37])[O:34][C@H:33]([CH3:38])[CH2:32]2)=[C:22]([F:30])[C:23]([F:29])=[C:24](/[CH:26]=[N:27]/O)[CH:25]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OC(=O)C)(=O)C>[Si:1]([O:18][CH2:19][C:20]1[C:21]([N:31]2[CH2:32][C@H:33]([CH3:38])[O:34][C@H:35]([CH3:37])[CH2:36]2)=[C:22]([F:30])[C:23]([F:29])=[C:24]([CH:25]=1)[C:26]#[N:27])([C:14]([CH3:16])([CH3:15])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of (E)-1-{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}-N-hydroxymethanimine (Intermediate 5, 8.0 g, 14.8 mmol) and acetic anhydride (10 mL) was stirred at 130° C. for 12 hours. the reaction mixture cooled to room temperature and concentrated, and the residue was purified over a silica gel flash column using a gradient of ethyl acetate in pet. ether to give the title compound as yellow solid. Yield: 6.5 g, (85%).

Workup

temperaturethe reaction mixture cooled to room temperature
concentrationconcentrated
customthe residue was purified over a silica gel flash column

Sources & evidence

ORD record: ord-a475c6dcf38e40c5bbdbee25b2d9e544
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658641B2

Reaction notes

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