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Undec-4-ene → HCID 54373433, compound

HRID 1756789
Notes
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Reaction equation

HRID 1756789 reaction equation
[NH2:1][C:2]1[C:3]([N:10]([CH3:12])[CH3:11])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH3:9].C([O:15][C:16]([NH:18][CH2:19][C@@H:20]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]2[O:32][CH2:33][O:34][C:27]=12)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=O)C.[CH3:35]CCCCCC=CCCC>O1CCOCC1>[CH2:33]1[O:32][C:28]2[C:27](=[C:26]([C@@H:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:19][NH:18][C:16]([NH:1][C:2]3[C:3]([N:10]([CH3:11])[CH3:12])=[N:4][CH:5]=[N:6][C:7]=3[O:8][CH2:9][CH3:35])=[O:15])[CH:31]=[CH:30][CH:29]=2)[O:34]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 136496Undec-4-eneHCID 104195636-methoxy-4-N,4-N-dimethylpyrimidine-4,5-diamineHCID 54392650HCID 54392650, compound

Product 1

HCID 54373433HCID 54373433, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.66 g of 5-amino-4-dimethylamino-6-methoxypyrimidine, 1.28 g of N-ethoxycarbonyl-(R)-2-(2, 3-methylenedioxyphenyl) heptylamine, 0.55 g of 1, 8-diazabicyclo [5, 4, 0] undec-7-ene and 10 ml of dioxane was stirred at 100° C. for 16 hours and the solvent evaporated. The residue was chromatographed on a silica gel column, eluting with ethyl acetate-n-hexane (2:1-3:1), and the product was dissolved in ether. The solution was washed with water and saturated saline in this order, dried over anhydrous sodium sulfate and the solvent evaporated. The residue was triturated with n-hexane to give 0.63 g of the titled compound.

Workup

  1. customthe solvent evaporated
  2. customThe residue was chromatographed on a silica gel column
  3. washeluting with ethyl acetate-n-hexane (2:1-3:1)
  4. dissolutionthe product was dissolved in ether
  5. washThe solution was washed with water and saturated saline in this order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent evaporated
  8. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-e41dc2650e004e7ca4d7022b86c1fc4b
Source dataset
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05442060

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes