1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86701169, compound

HRID 572127Notes

Reaction equation

HRID 572127 reaction equation
C1CN([P+]([O:17][N:18]2[N:26]=[N:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1CC[N:42]2[C:37](=[N:38][CH2:39][CH2:40][CH2:41]2)CC1>C(#N)C>[N:18]1([O:17][C:39]2[C:40]3[N:18]=[CH:19][CH:20]=[CH:21][C:41]=3[N:42]=[CH:37][N:38]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:25]=[N:26]1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724699PyBOP

Product 1

HCID 86701169HCID 86701169, compoundYield 136.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of this material (10 g, 68.0 mmol) and PyBOP (38.9 g, 74.8 mmol) in acetonitrile (250 mL) was treated with DBU (12.2 mL, 81.6 mmol) and stirred for 2.5 h. The reaction mixture was filtered, and the precipitate was washed with diethyl ether (3×50 mL) and dried under vacuum. The title compound (13.51 g, 75%) was obtained as a cream-coloured solid. δH (DMSO-d6) 9.28 (dd, J 4.2, 1.6 Hz, 1H), 8.82 (s, 1H), 8.59 (dd, J 8.6, 1.5 Hz, 1H), 8.24-8.18 (m, 2H), 7.88-7.85 (m, 1H), 7.69-7.64 (m, 1H), 7.60-7.54 (m, 1H). LCMS (ES+) 265 (M+H)+, RT 1.23 minutes.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe precipitate was washed with diethyl ether (3×50 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-2d865ec4ef634390b51ef488f41aa3ac
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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