1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22929892, compound

HRID 1295937Notes

Reaction equation

HRID 1295937 reaction equation
[CH3:1][NH:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[C:7]([CH2:12]O)=[CH:6][C:5]=1[N:14]([CH3:16])[CH3:15].N12CCCN=C1CCCCC2.C1(P([N:43]=[N+:44]=[N-:45])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[CH3:1][NH:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[C:7]([CH2:12][N:43]=[N+:44]=[N-:45])=[CH:6][C:5]=1[N:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 22929785HCID 22929785, compound

Product 1

HCID 22929892HCID 22929892, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving N1-methyl-5-cyano-2-(dimethylamino)-4-(hydroxymethyl)benzamide (849 mg, 3.6 mmol) in tetrahydrofuran (20 ml), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.77 ml, 5.1 mmol) and diphenylphosphoryl azide (1.1 ml, 5.1 mmol) were added and the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (755 mg) as a faint yellow powder. (80% yield)

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a909580e663e43d7a9c1609d803862e3
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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