Dimethylformamide → HCID 18630661, compound

HRID 582572Notes

Reaction equation

HRID 582572 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+].Cl[CH2:29]/[CH:30]=[CH:31]\[CH2:32]Cl.C[N:35](C)C=O>>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:13]([N:12]2[CH:30]([CH:31]=[CH2:32])[CH2:29][N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1](=[NH:35])[NH2:2])[CH:4]=3)[C:10]2=[O:11])[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 64321151,4-Dichloro-cis-2-butene2×HCID 18630658HCID 18630658, compound

Product 1

HCID 18630661HCID 18630661, compound

Procedure

A mixture of N-(3-cyanophenyl)-N'-(1-(t-butoxycarbonyl)-piperidin-4-yl)urea (0.50 g, 1.45 mmol) and sodium hydride (0.20 g of a 60% suspension in mineral oil, 8.3 mmol) in dimethylformamide was stirred at ambient temperature for 30 min. then cis-1,4-dichloro-2-butene (0.18 g, 1.44 mmol) was added. This mixture was heated at 70° C. for 4 h, after which an addition 0.2 g of 60% sodium hydride and 0.04 g of cis-1,4-dichloro-2-butene was added. The mixture was heated at 70° C. for an addition 2 h during which the remaining starting material was consumed. The reaction was diluted with brine (50 ml) and extracted with ethyl acetate (3×). The ethyl acetate extracts were washed with brine, then dried (Na2SO4) and evaporated. The residue was purified by flash chromatography on silica gel, eluting with 2:1 hexane:ethyl acetate to give 0.20 g of 1-(1-t-butoxycarbonylpiperidin-4-yl)-3-(3-amidinophenyl)-5-ethenyl-2-imidazolidinone; LRMS (M+H)+ m/z 397.

Workup

  1. temperatureThis mixture was heated at 70° C. for 4 h
  2. additionwas added
  3. temperatureThe mixture was heated at 70° C. for an addition 2 h during which the
  4. customwas consumed
  5. additionThe reaction was diluted with brine (50 ml)
  6. extractionextracted with ethyl acetate (3×)
  7. washThe ethyl acetate extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customThe residue was purified by flash chromatography on silica gel
  11. washeluting with 2:1 hexane

Sources & evidence

ORD record
ord-d1c650bccd76452190310e0e3cc2369a
Source dataset
uspto-grants-1999_07
Patent number
US05925635

Reaction notes

Loading…