1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178517555, compound

HRID 1772716Notes

Reaction equation

C([O:3][C:4]([O:6]/[N:7]=[C:8](/[NH2:42])\[C:9]1[CH:14]=[C:13]([C:15]2[N:20]3[CH:21]=[C:22](/[CH:24]=[CH:25]/[C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[N:23]=[C:19]3[C:18]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[N:17][CH:16]=2)[CH:12]=[N:11][CH:10]=1)=O)C.C1CCN2C(=NCCC2)CC1>C(#N)C>[O:39]1[CH2:38][CH2:37][N:36]([C:18]2[C:19]3[N:20]([CH:21]=[C:22](/[CH:24]=[CH:25]/[C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[N:23]=3)[C:15]([C:13]3[CH:14]=[C:9]([C:8]4[N:42]=[C:4]([OH:3])[O:6][N:7]=4)[CH:10]=[N:11][CH:12]=3)=[CH:16][N:17]=2)[CH2:41][CH2:40]1

Participants

Conditions

Temperature: 100 °C

Procedure

Compound 77a (26.5 mg, 0.469 mmol) was placed in an 8 mL vial equipped with a stir bar. ACN (1 mL) and DBU (0.358 μL, 0.00235 mmol) were added. The reaction was stirred at 100° C. for 18 h and then cooled to rt. The precipitate was collected by filtration and then the solid was washed with ACN (2×5 mL). The residual solvent was removed under reduced pressure to afford the title compound 28. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 9.06 (d, J=2.0 Hz, 1H), 8.85 (d, J=2.0 Hz, 1H), 8.32-8.37 (m, 2H), 8.27 (s, 1H), 7.97 (d, J=8.6 Hz, 1H), 7.94 (d, J=7.6 Hz, 1H), 7.87 (d, J=3.5 Hz, 1H), 7.90 (d, J=4.0 Hz, 1H), 7.75 (t, J=7.1 Hz, 1H), 7.66 (d, J=16.2 Hz, 1H), 7.56 (t, J=7.3 Hz, 1H), 7.52 (s, 1H), 4.29-4.39 (m, 4H), 3.81-3.87 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C28H22N8O3: 519.2 (M+H). found: 519.3.

Workup

customvial equipped with a stir bar
temperaturecooled to rt
filtrationThe precipitate was collected by filtration
washthe solid was washed with ACN (2×5 mL)
customThe residual solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-2bab59b20a8a42eda9018c240614421f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249163B2

Reaction notes

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