HCID 86659827, compound → HCID 46840314, compound

HRID 1846381Notes

Reaction equation

HRID 1846381 reaction equation
[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[N:30](C)C)=[C:24]([N+]([O-])=O)[CH:23]=2)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2]>CCO.CN(C=O)C>[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:27]=[C:26]3[C:25]([CH:28]=[CH:29][NH:30]3)=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 86659827HCID 86659827, compound

Product 1

HCID 46840314HCID 46840314, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

A solution of (E)-3-(4-sec-butylphenyl)-2-(4-(2-(dimethylamino)vinyl)-3-nitrophenyl)quinazolin-4(3H)-one (0.565 g, 1.20 mmol) in a 3:1 mixture of EtOH/DMF (25 mL) was flushed with N2. Pd/C (0.060 g, 10 wt %) was added and flushed with H2 for 2.5 hours. After filtering through diatomaceous earth, the filtrate was concentrated. Purification was effected by flash chromatography on silica gel, eluting with 5% to 75% EtOAc in heptane, Further purification was effected by reverse-phase chromatography, eluting with 10% to 90% CH3CN in H2O with 0.1% TFA. The desired fractions were collected, basified, and extracted with CH2Cl2, to afford the title compound as a white solid (0.040 g, 8%). 1H-NMR (300 MHz, DMSO-d6): δ11.27 (s, 1H), 8.18 (d, J=8.0 Hz, 1H), 7.87-7.90 (m 1H), 7.75 (d, J=7.8 Hz, 1H), 7.56-7.59 (m, 1H), 7.50 (s, 1H), 7.37 (d, J=2.6 Hz, 1H), 7.27 (d, J=8.3 Hz, 1H), 7.19-7.22 (m, 2H), 7.08-7.10 (m, 2H), 6.89-6.92 (m, 1H), 6.34 (s, 1H), 2.51-2.61 (m, 1H), 1.33-1.20 (m, 2H), 1.11 (d, J=6.9 Hz, 3H), 0.59 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 394 (M+H)+.

Workup

  1. customwas flushed with N2
  2. additionPd/C (0.060 g, 10 wt %) was added
  3. customflushed with H2 for 2.5 hours
  4. filtrationAfter filtering through diatomaceous earth
  5. concentrationthe filtrate was concentrated
  6. customPurification
  7. washeluting with 5% to 75% EtOAc in heptane, Further purification
  8. washeluting with 10% to 90% CH3CN in H2O with 0.1% TFA
  9. customThe desired fractions were collected
  10. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-1c6fd51ef61d497fb3f92788685d92aa
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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