HCID 19087863, compound → HCID 19087858, compound

HRID 1464343Notes

Reaction equation

HRID 1464343 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[N:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32]([CH2:33][O:34][CH3:35])[N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=1)[C:5]2=[O:36]>C1COCC1.N1C=CC=CC=1.C(OCC)(=O)C>[CH3:35][O:34][CH2:33][N:32]1[C:28]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:19]2[CH:18]=[CH:17][C:16]([CH2:15][N:6]3[C:5](=[O:36])[C:4]4[C:9](=[CH:10][CH:11]=[C:2]([O:1][C:5](=[O:36])[NH:6][CH2:7][CH2:12][CH3:13])[CH:3]=4)[N:8]=[C:7]3[CH2:12][CH2:13][CH3:14])=[CH:21][CH:20]=2)=[N:29][N:30]=[N:31]1

Participants

5

Reactant 1

HCID 19087863HCID 19087863, compound

Product 1

HCID 19087858HCID 19087858, compoundYield 158.7%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-hydroxy-3-[[2'-(N-methoxymethyltetrazol-5-yl)biphenyl-4-yl]methyl]-2-propyl-4(3H)-quinazolinone (0.15 g) propyl isocyanate (0.9 ml) in a mixture of THF (5 ml) and pyridine (2 ml) was heated under reflux for 6 days. The reaction mixture was diluted with ethyl acetate and the solution was washed with 1N hydrochloric acid and water, dried and concentrated to dryness. The residue was purified by column chromatography on silica gel to give a pale yellow powder (0.14 g, 79%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 days
  3. washthe solution was washed with 1N hydrochloric acid and water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-83e00b5c013f416a86d3d773e8f2f565
Source dataset
uspto-grants-1994_04
Patent number
US05304565

Reaction notes

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