Benzylamine → HCID 135838187, compound

HRID 1884004Notes

Reaction equation

HRID 1884004 reaction equation
[Br:1][C:2]1[C:15]2[CH:14]=[CH:13][C:12]3[N:11]=[C:10](NC(=O)C(C)(C)C)[NH:9][C:8](=[O:23])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CCOCC>[CH2:24]([NH:31][C:10]1[NH:9][C:8](=[O:23])[C:7]2[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[C:15]=3[CH:14]=[CH:13][C:12]=2[N:11]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 135838160HCID 135838160, compound

Product 1

HCID 135838187HCID 135838187, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of N-(7-bromo-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide (0.3 g, 0.8 mmole) and benzylamine (10 ml) was stirred and heated at reflux under a nitrogen atmosphere for 18 hours. The cooled reaction mixture was then mixed with 4 volumes of ether to cause precipitation of the product. The precipitate was filtered and recrystallized from methanol to give 3-(benzylamino)-7-bromobenzo-[f]quinazolin-1(2H)-one as an off-white solid. (0.11 g, 37%) 1H NMR (DMSO-d6, 200 MHz) δ: 4.62 (d, J=5.7 Hz, 2H, CH2); 7.02 (m, 1H, benzyl-NH); 7.20-7.55 (m, 7H, Ar); 7.79 (dd, J=7.5, 1.1 Hz, 1H, Ar); 8.30 (d, J=9.2 Hz, 1H, Ar); 9.74 (d, J=8.6 Hz, 1H, Ar); 11.2 (br s, 1H, pyr-NH).

Workup

  1. temperatureheated
  2. temperatureat reflux under a nitrogen atmosphere for 18 hours
  3. customThe cooled reaction mixture
  4. customprecipitation of the product
  5. filtrationThe precipitate was filtered
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5037ae869f174c5f959631af7ccb44d2
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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