HCID 86659826, compound → HCID 46840312, compound

HRID 1846378Notes

Reaction equation

HRID 1846378 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]2[C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[N:27](C)C)=[C:21]([N+]([O-])=O)[CH:20]=2)=[CH:4][CH:3]=1>CCO.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]2[C:19]2[CH:24]=[C:23]3[C:22]([CH:25]=[CH:26][NH:27]3)=[CH:21][CH:20]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86659826HCID 86659826, compound

Product 1

HCID 46840312HCID 46840312, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

A solution of (E)-3-(4-chlorophenyl)-2-(4-(2-(dimethylamino)vinyl)-3-nitrophenyl)quinazolin-4(3H)-one (0.340 g, 0.76 mmol) in a 3:1 mixture of EtOH/DMF (50 mL) was flushed with N2. Pd/C (0.034 g, 10 wt %) was added the reaction was flushed with H2 for 1.5 hours. After filtering through diatomaceous earth, the filtrate was concentrated. Purification by flash chromatography on silica gel, eluting with 5% to 70% EtOAc in heptane, afforded the title compound as a white solid (0.105 g, 37%). 1H-NMR (300 MHz, DMSO-d6, mixture of rotamers): δ11.34 (s, 0.5H), 11.25 (s, 0.5H), 8.16-8.29 (m, 1H), 7.86-8.00 (m, 1H), 7.71-7.82 (m, 1H), 7.49-7.67 (m, 3H), 7.29-7.48 (m, 5H), 6.87-7.05 (m, 1H), 6.37-6.42 (m, 0.5H), 6.25-6.26 (m, 0.5H). MS (APCI) m/z: 372 (M+H)+.

Workup

  1. customwas flushed with N2
  2. additionPd/C (0.034 g, 10 wt %) was added the reaction
  3. customwas flushed with H2 for 1.5 hours
  4. filtrationAfter filtering through diatomaceous earth
  5. concentrationthe filtrate was concentrated
  6. customPurification by flash chromatography on silica gel
  7. washeluting with 5% to 70% EtOAc in heptane

Sources & evidence

ORD record
ord-55ad54801b3c49feaf5c458d752f702d
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

Loading…