1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 131394745, compound

HRID 1049142Notes

Reaction equation

[CH3:1][C:2]1[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)=[CH:5][NH:4][N:3]=1.[C:16]([CH:18]=[C:19]1[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20]1)#[N:17].N12CCCN=C1CCCCC2>C(#N)C>[C:16]([CH2:18][C:19]1([N:4]2[CH:5]=[C:6]([B:7]3[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]3)[C:2]([CH3:1])=[N:3]2)[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20]1)#[N:17]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.06 g, 5.10 mmol), tert-butyl 3-(cyanomethylene)azetidine-1-carboxylate (1.00 g, 5.15 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.38 mL, 2.6 mmol) in acetonitrile (20 mL) was heated at 60° C. for 2 h. After cooling, the solvent was removed under reduced pressure. The residue was purified by flash chromatography on a silica gel column eluting with ethyl acetate in hexanes (0-60%) to afford the desired product. LCMS cacld. for C16H24BN4O4 (M−55)+: m/z=347.2. Found: 347.1.

Workup

temperatureAfter cooling
customthe solvent was removed under reduced pressure
customThe residue was purified by flash chromatography on a silica gel column
washeluting with ethyl acetate in hexanes (0-60%)

Sources & evidence

ORD record: ord-4cf9cdc0c6e9495eab2e64a7340175d6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382231B2

Reaction notes

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