HCID 136415077, compound → HCID 135939081, compound

HRID 591861Notes

Reaction equation

HRID 591861 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:15]2[NH:24][C:23](=[O:25])[C:22]3[C:17](=[CH:18][C:19]([O:28][CH3:29])=[CH:20][C:21]=3[O:26][CH3:27])[N:16]=2)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1)=[N+]=[N-].[C:30]([OH:33])(=S)[CH3:31]>>[CH3:27][O:26][C:21]1[CH:20]=[C:19]([O:28][CH3:29])[CH:18]=[C:17]2[C:22]=1[C:23](=[O:25])[NH:24][C:15]([C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([O:13][CH3:14])[CH:10]=1)[O:6][CH2:5][CH2:4][NH:1][C:30](=[O:33])[CH3:31])=[N:16]2

Participants

3

Reactant 2

HCID 136415077HCID 136415077, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 135939081HCID 135939081, compound

Procedure

2-[3-(2-Azido-ethoxy)-5-methoxy-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one (90 mg, 0.22 mmol) was taken in thioacetic acid (2 mL) and the reaction mixture was stirred at room temperature for 2 hours. Thioacetic acid was removed under reduced pressure, and the residue was purified by column chromatography (silica gel 230-400 mesh; 3.5% methanol in dichloromethane as eluent) to give the title compound as a white solid. Yield: 45 mg (49%). MP 264-265° C. 1H NMR (400 MHz, DMSO-d6): δ 12.05 (s, 1H), 8.13 (t, J=5.86 Hz, 1H), 7.39 (d, J=1.56 Hz, 2H), 6.76 (d, J=2.34 Hz, 1H), 6.69 (t, J=2.15 Hz, 1H), 6.55 (d, J=2.34 Hz, 1H), 4.07 (t, J=5.67 Hz, 2H), 3.90 (s, 3H), 3.85 (s, 3H), 3.83 (s, 3H), 3.43 (q, J=5.47 Hz, 2H), 1.84 (s, 3H). MS (ES+) m/z: 414.11 (M+1).

Workup

  1. customThioacetic acid was removed under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel 230-400 mesh; 3.5% methanol in dichloromethane as eluent)

Sources & evidence

ORD record
ord-8209a409242b420a805eeda393b308e9
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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