HCID 11317628, compound → HCID 178469657, compound

HRID 2119329Notes

Reaction equation

HRID 2119329 reaction equation
[CH2:1]([N:8]([CH3:35])[C:9]1[CH:27]=[C:26]([CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:25]=[CH:24][C:10]=1[NH:11][CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14](OCC)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(OC2C=CC=CC=2)C=CC=CC=1.C1(C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:35])[C:9]1[CH:27]=[C:26]([CH2:28][N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)[CH:25]=[C:24]2[C:10]=1[N:11]=[CH:12][C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]2[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 11317628HCID 11317628, compound

Product 1

HCID 178469657HCID 178469657, compoundYield 50.7%

Reagents, catalysts & solvents 3

HCID 7095BiphenylSolventHCID 7583Diphenyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl 2-{[2-[benzyl(methyl)amino]-4-(4-morpholinylmethyl)anilino]-methylene}malonate (3.7 g, 7.7 mmol) is stirred in a mixture of phenyl ether (9 g) and biphenyl (3 g) at 260 ° C. A slow stream of nitrogen is passed through the solution to remove volatile materials produced in the reaction. The reaction is stopped as soon as HPLC shows that conversion of the starting material to product is complete (60 min). After cooling, the reaction mixture is applied in ethyl acetate to a silica gel column which is eluted with ethyl acetate (400 mL) to remove phenyl ether and biphenyl. The column is then eluted with 5-10% methanol/chloroform and the product obtained is recrystallized from ethyl acetate/hexane (3:1, 15 mL) to give 1.70 g of the title compound.

Workup

  1. customto remove volatile materials
  2. customproduced in the reaction
  3. custom(60 min)
  4. temperatureAfter cooling
  5. washis eluted with ethyl acetate (400 mL)
  6. customto remove phenyl ether and biphenyl
  7. washThe column is then eluted with 5-10% methanol/chloroform
  8. customthe product obtained
  9. customis recrystallized from ethyl acetate/hexane (3:1, 15 mL)

Sources & evidence

ORD record
ord-7f3ddc9aab094a2c872ff142589aa1da
Source dataset
uspto-grants-2004_02
Patent number
US06686356B2

Reaction notes

Loading…