Sodium Hydroxide → 1,3-Bis{[7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]methyl}urea

HRID 711405Notes

Reaction equation

HRID 711405 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[O:16])[NH:14][CH2:13][CH:12]([CH2:17][NH:18][C:19]([N:21]=[N+]=[N-])=[O:20])[N:11]3[CH:24]=2)[CH:5]=[CH:6][CH:7]=1.[OH-:25].[Na+]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[O:16])[NH:14][CH2:13][CH:12]([CH2:17][NH:18][C:19]([NH:21][CH2:17][CH:12]4[N:11]5[CH:24]=[C:8]([C:4]6[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=6)[CH:9]=[C:10]5[C:15](=[O:25])[NH:14][CH2:13]4)=[O:20])[N:11]3[CH:24]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86732553{[7-(3-Chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]methyl}carbamic azide

Product 1

HCID 867325541,3-Bis{[7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]methyl}ureaYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step b 71 mg (0.206 mmol) of {[7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]methyl}carbamic azide were dissolved in 10 ml of dry THF, NaOH 1N (2 ml) was added and the mixture was stirred at room temperature for 30 minutes. The reaction was diluted with EtOAc and extracted with water, the organic layer was mixed with HCl 2N (5 ml) for 10 minutes, and then discarded; the aqueous solution was brought to pH 10 with NaOH 23% (10 ml) and portioned between EtOAc (10 ml) and THF (10 ml). The organic layers were washed with brine, dried over Na2SO4 and evaporated under reduced pressure to give the title compound 50 mg (89%) as a light yellow solid.

Workup

  1. extractionextracted with water
  2. additionthe organic layer was mixed with HCl 2N (5 ml) for 10 minutes
  3. washThe organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6704609abe62415398b8a600807e0b22
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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