HCID 68803139, compound → HCID 59993166, compound

HRID 238210Notes

Reaction equation

HRID 238210 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]([C:20]3[N:29]([CH3:30])[C:28](=[O:31])[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([N+:32]([O-])=O)[CH:26]=4)[N:21]=3)[CH3:19])[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1>[Cl-].[Cl-].[Zn+2].C(O)C>[NH2:32][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([CH:18]([N:15]1[CH2:14][CH2:13][N:12]([S:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[CH2:17][CH2:16]1)[CH3:19])[N:29]([CH3:30])[C:28]2=[O:31]

Participants

4

Reactant 1

HCID 68803139HCID 68803139, compound

Product 1

HCID 59993166HCID 59993166, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent

Procedure

To the 15 ml ethanol solution of 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-6-nitro-3H-quinazolin-4-one (560.0 mg, 1.14 mmol) was added ZnCl2 (1.08 g, 5.7 mmol). The reaction was refluxed for 2 hours with vigorous agitation by a magnetic stirrer. The mixture was cooled to room temperature, the solvent was removed by reduce pressure and extracted with Na2CO3 aqueous and ethyl acetate, dried over anhydrous MgSO4, and concentrated by rotary evaporation. Purification was accomplished by HPLC (Gilson-215, 0.035% TFA in acetonitrile and 0.05% water as mobile phase). The product was collected and dried under reduced pressure to give 6-Amino-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-3H-quinazolin-4-one (Yield 427.3 mg, 81.9%). 1H NMR (400 MHz, DMSO-d6): δ 1.72 (d, 3H, J=6.57 Hz), 3.44-3.29 (m, 4H), 3.62-3.50 (m, 4H), 3.65 (s, 3H), 3.93 (s, 3H), 4.70 (q, 1H, J=12.88, 6.82 Hz), 7.19 (d, 2H, J=8.84 Hz), 7.49 (dd, 1H, J=8.84, 2.53 Hz), 7.65 (d, 1H, J=8.59 Hz), 7.81-7.77 (m, 3H). MS m/z calc. 457.2 found (ESI); 458.2 (M+1)+. Retention time 2.28 minutes.

Workup

  1. temperatureThe reaction was refluxed for 2 hours with vigorous agitation by a magnetic stirrer
  2. customthe solvent was removed
  3. extractionextracted with Na2CO3 aqueous and ethyl acetate
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated by rotary evaporation
  6. customPurification
  7. customThe product was collected
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-91dcb802255e4d2589859954fe95df83
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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