Triethylamine → HCID 136054862, compound

HRID 374771Notes

Reaction equation

HRID 374771 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][CH2:22][CH3:23])=[C:6]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[C:11]([CH3:19])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=1.[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([C:31](=[O:34])[CH:32]=[CH2:33])[CH2:27][CH2:26]1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(#N)C>[CH3:19][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[N:9]=[C:8]([C:6]1[CH:7]=[C:2]([CH2:33][CH2:32][C:31]([N:28]3[CH2:27][CH2:26][N:25]([CH3:24])[CH2:30][CH2:29]3)=[O:34])[CH:3]=[CH:4][C:5]=1[O:20][CH2:21][CH2:22][CH3:23])[NH:17][C:16]2=[O:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 13742939ACRYLAMIDO BUFFERHCID 136110484HCID 136110484, compound

Product 1

HCID 136054862HCID 136054862, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 2-(5-bromo-2-n-propoxyphenyl)-8-methylquinazolin-4(3H)-one (Preparation 11; 0.5 g, 0.0013 mol), 1-methyl-4-propenoylpiperazine (Makromol. Chem., 1984, 185, 1525; 0.24 g, 0.0015 mol), palladium diacetate (0.175 g, 0.00077 mol), tri-o-tolylphosphine (0.30 g, 0.001 mol), triethylamine (1 ml) and acetonitrile (25 ml) was heated under reflux under a nitrogen atmosphere for 4 days. The cool mixture was filtered and the filtrate evaporated to dryness under vacuum. The residue was suspended in saturated aqueous sodium carbonate solution (25 ml), the resulting solution extracted with dichloromethane (50 ml) and the organic extract washed with brine (2×30 ml), dried (Na2SO4) and evaporated under vacuum. Chromatography of the residue on silica gel (10 g), using a methanol in dichloromethane elution gradient (0-4%), gave the title compound which crystallized from hexane-ethyl acetate as a pale pink solid (0.072 g, 12%), m.p. 184°-185° C. Found: C,89.96; H,6.64; N,12.49. C26H30N4O3 requires C,69.93; N,6.77; N,12.55%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under a nitrogen atmosphere for 4 days
  3. filtrationThe cool mixture was filtered
  4. customthe filtrate evaporated to dryness under vacuum
  5. extractionthe resulting solution extracted with dichloromethane (50 ml)
  6. extractionthe organic extract
  7. washwashed with brine (2×30 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated under vacuum
  10. washa methanol in dichloromethane elution gradient (0-4%)

Sources & evidence

ORD record
ord-4c401ccec6454d8fabd8170f37105972
Source dataset
uspto-grants-1996_01
Patent number
US05482941

Reaction notes

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