1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 89767940, compound

HRID 591481Notes

Reaction equation

HRID 591481 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])=[CH:10][C:5]=2[S:4][C:3]=1[C:21]([NH2:23])=[O:22].C1CCN2C(=NCCC2)CC1.C(N)(=[S:37])C>CN(C=O)C.Cl>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH2:12][O:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2]([SH:37])=[C:3]([C:21]([NH2:23])=[O:22])[S:4][C:5]=2[CH:10]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2723949ThioacetamideHCID 89767843HCID 89767843, compound

Product 1

HCID 89767940HCID 89767940, compoundYield 21.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 3-chloro-6-((2,4-dichlorobenzyl)oxy)-1-benzothiophene-2-carboxamide (193.6 mg) in DMF (dry) (2.5 mL) were added DBU (0.225 mL) and thioacetamide (113 mg). The mixture was stirred at 80° C. for 5.5 h. After cooling, the mixture was diluted with 1N HCl and extracted with EtOAc. The combined organic layer was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The precipitate was washed with hexane and THF to give the title compound (41.6 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washThe precipitate was washed with hexane and THF

Sources & evidence

ORD record
ord-83f6ddd1d5ad4db1ae251e0d95572eb3
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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