1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178469451, compound

HRID 1796624Notes

Reaction equation

HRID 1796624 reaction equation
C(O[C:4]([C:6]1[N:7]([NH2:18])[CH:8]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]=1[O:11][CH3:12])=[O:5])C.CO[CH:21](OC)[CH2:22][C:23]#[N:24].CC1C=CC(S(O)(=O)=O)=CC=1.O.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[CH2:16]([O:15][C:13]([C:9]1[C:10]([O:11][CH3:12])=[C:6]2[C:4]([OH:5])=[C:22]([C:23]#[N:24])[CH:21]=[N:18][N:7]2[CH:8]=1)=[O:14])[CH3:17]

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 937313,3-DimethoxypropiononitrileHCID 521998p-Toluenesulfonic acid monohydrateHCID 129859111-Amino-3-methoxy-1H-pyrrole-2,4-dicarboxylic acid diethyl ester

Product 1

HCID 178469451HCID 178469451, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of amine 393E (0.34 g, 1.33 mmol) in toluene (2.6 ml) was added 3,3-dimethoxy-propionitrile (0.4 ml, 2.66 mmol) and TsOH.H2O (50 mg, 0.266 mmol), the mixture was heated at 80° C. for 4 h, then DBU (0.404 mg, 2.66 mmol) was added, and heated for another 0.5 h. The residue was purified by silica gel flash column chromatography to give 0.46 g of crude 393F (10% MeOH—CH2Cl2).

Workup

  1. temperatureheated for another 0.5 h
  2. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-25d50691b1e147ae9afdaa799580dd03
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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