1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67755339, compound

HRID 2372379Notes

Reaction equation

HRID 2372379 reaction equation
[CH3:1][NH:2][C:3](=[O:20])[CH2:4][C:5]1[N:6]2[CH2:12][CH:11]([CH3:13])[C:10]([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])=[C:7]2[S:8][CH:9]=1.C1CCN2C(=NCCC2)CC1>C(Cl)(Cl)Cl.CO>[CH3:1][NH:2][C:3](=[O:20])[CH:4]=[C:5]1[CH2:9][S:8][C:7]2=[C:10]([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])[CH:11]([CH3:13])[CH2:12][N:6]12

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19903349N-Methyl-(7-isopropoxycarbonyl-6-methyl-5,6-dihydropyrrolo[2,1-b]thiazol-3-yl)acetamide

Product 1

HCID 67755339HCID 67755339, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

2.0 g of N-methyl-(7-isopropoxycarbonyl-6-methyl-5,6- dihydropyrrolo[2,1-b]thiazol-3-yl)acetamide was dissolved in a solvent mixture of 60 ml of chloroform and 6 ml of methanol. 0.3 g of 1,8-diazabicyclo[5.4.0]-7-undecene was added thereto and the mixture was stirred at 20° C. for 15 hours. The reaction mixture was then washed with 20 ml of 5% aqueous acetic acid, a 0.5% aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride. The chloroform layer was dried over anhydrous sodium sulfate. After distilling off the chloroform, the obtained crude crystals were recrystallized from ethanol to thereby give 1.5 g of the title compound.

Workup

  1. washThe reaction mixture was then washed with 20 ml of 5% aqueous acetic acid
  2. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  3. distillationAfter distilling off the chloroform
  4. customthe obtained crude crystals
  5. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-6ffb081e98734b2ca9c2636d5126888f
Source dataset
uspto-grants-1992_03
Patent number
US05098919

Reaction notes

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