Diisopropylethylamine → HCID 86658132, compound

HRID 245530Notes

Reaction equation

[C:1](=[O:21])([O:7][C:8]1[C:12]2[CH:13]=[C:14]([CH:19]=[O:20])[C:15](F)=[C:16]([F:17])[C:11]=2[O:10][N:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].CCN(C(C)C)C(C)C.[CH3:31][C@H:32]1[O:37][C@@H:36]([CH3:38])[CH2:35][NH:34][CH2:33]1>C(#N)C>[C:1](=[O:21])([O:7][CH:8]1[C:12]2[CH:13]=[C:14]([CH:19]=[O:20])[C:15]([N:34]3[CH2:33][C@H:32]([CH3:31])[O:37][C@H:36]([CH3:38])[CH2:35]3)=[C:16]([F:17])[C:11]=2[O:10][NH:9]1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To an ice cooled and stirred solution of tert-butyl 6,7-difluoro-5-formyl-1,2-benzisoxazol-3-yl carbonate (Intermediate 531, 3.0 g, 10.0 mmol) in anhydrous acetonitrile was added DIPEA (2.56 g, 20.0 mmol) followed by cis 2,6-dimethylmorpholine (1.27 g, 11.0 mmol) and the mixture heated at 80° C. for 12 hours. It was cooled to room temperature and concentrated. The residue was dissolved in ethyl acetate, washed with water followed by brine and then dried over anhydrous sodium sulfate. It was filtered and the filtrate evaporated under reduced pressure. The residue was purified on a silica gel column using a gradient of ethyl acetate in pet.ether to give product as a solid. Yield: 2.9 g (74%).

Workup

temperatureIt was cooled to room temperature
concentrationconcentrated
dissolutionThe residue was dissolved in ethyl acetate
washwashed with water
dry with materialdried over anhydrous sodium sulfate
filtrationIt was filtered
customthe filtrate evaporated under reduced pressure
customThe residue was purified on a silica gel column
customether to give product as a solid

Sources & evidence

ORD record: ord-7747aa1c15fa4100bec5b583e1a629a8
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658641B2

Reaction notes

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