Trimethylsilyl cyanide → N-((8-Benzyl-7-(3-cyanooxetan-3-ylamino)-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)-1-cyclopropylmethanesulfonamide

HRID 82875Notes

Reaction equation

[NH2:1][CH:2]1[CH:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[CH:9]=[C:8]([CH2:19][NH:20][S:21]([CH2:24][CH:25]3[CH2:27][CH2:26]3)(=[O:23])=[O:22])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[O:28]1[CH2:31][C:30](=O)[CH2:29]1.C[Si]([C:37]#[N:38])(C)C>C(OCC)(=O)C>[CH2:12]([CH:11]1[C:10]2[CH:9]=[C:8]([CH2:19][NH:20][S:21]([CH2:24][CH:25]3[CH2:27][CH2:26]3)(=[O:23])=[O:22])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3][CH:2]1[NH:1][C:30]1([C:37]#[N:38])[CH2:31][O:28][CH2:29]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 200 °C

Procedure

N-((7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)-1-cyclopropylmethanesulfonamide (0.083 g, 0.216 mmol) and 3-oxetanone (0.031 g, 0.432 mmol) were sealed in a vial and heated at 200° C. for 2 minutes. Trimethylsilyl cyanide (0.58 mL, 0.432 mmol) was added, the vial was resealed and the mixture was heated again at 200° C. for 2 minutes. The mixture was diluted with ethyl acetate (40 mL) and washed with 1N NaOH (1×20 mL) and brine (1×20 mL). The organic extract was collected, dried on MgSO4 and evaporated under reduced pressure to give a brown oil. The residue was purified by flash-chromatography on silica gel (100% heptane then up to 60% ethyl acetate in n-heptane). (24.9 mg, 0.048 mmol, 22.3%).

Workup

temperaturethe mixture was heated again at 200° C. for 2 minutes
washwashed with 1N NaOH (1×20 mL) and brine (1×20 mL)
extractionThe organic extract
customwas collected
customdried on MgSO4
customevaporated under reduced pressure
customto give a brown oil
customThe residue was purified by flash-chromatography on silica gel (100% heptane

Sources & evidence

ORD record: ord-b5e5ad11638c43eea3379fa0b04791d8
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846741B2

Reaction notes

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