Nitrogen → 10-bromo-2,3,4,5-tetrahydro-[1,3]diazepino[2,1-b]quinazolin-7(1H)-one

HRID 1619367Notes

Reaction equation

HRID 1619367 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4](/[N:12]=[C:13]2\C(Cl)=NSS\2)[CH:3]=1.[CH2:19]([NH2:24])[CH2:20][CH2:21][CH2:22][NH2:23].N#N>C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:8])[N:23]3[CH2:22][CH2:21][CH2:20][CH2:19][NH:24][C:13]3=[N:12]2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 1045PutrescineHCID 178497427HCID 178497427, compound

Product 1

HCID 13635994910-bromo-2,3,4,5-tetrahydro-[1,3]diazepino[2,1-b]quinazolin-7(1H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (E)-methyl 4-bromo-2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)benzoate (100 mg, 0.27 mmol, 1 eq) in THF was added butane-1,4-diamine (0.027 mL, 0.27 mmol, 1 eq) dropwise under N2 and the reaction was heated at reflux for 3 hours. After it was cooled to rt, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give the desired product, which was purified by silica gel chromatography. MS (ESI): 294, 296 (MH+).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 3 hours
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c888ba10aa904f6db10a552e4f2ec2d6
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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