Ethylenediamine → HCID 11695873, compound

HRID 1365062Notes

Reaction equation

HRID 1365062 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1)=O.[CH2:25]([NH2:28])[CH2:26][NH2:27]>C(O)C>[N+:22]([C:18]1[CH:17]=[C:16]([C:14]2[C:3]3[CH:4]=[C:5]([C:8]4[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=4)[CH:6]=[CH:7][C:2]=3[NH:28][CH2:25][CH2:26][N:27]=2)[CH:21]=[CH:20][CH:19]=1)([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 57732421HCID 57732421, compound

Product 1

HCID 11695873HCID 11695873, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

A 5 mL microwave tube was charged with [2-fluoro-5-(4-pyridinyl)phenyl](3-nitrophenyl)methanone (100 mg), ethanol and ethylenediamine (100 mg) then heated to 180° C. for 600 s using microwave irradiation. The reaction was concentrated to dryness and residue was taken up in water then extracted with methylene chloride. The extracts were dried over magnesium sulfate, filtered and concentrated to an oil. Silica gel purification followed by trituration with ether provided 5-(3-nitrophenyl)-7-(4-pyridinyl)-2,3-dihydro-1H-1,4-benzodiazepine (60 mg) as a yellow powder. H1 NMR (d6-dmso): 8.42 (d, 2H), 8.28 (s, 1H), 8.27 (d, 1H), 7.84 (d, 1H), 7.66 (m, 2H), 7.38 (d, 2H), 7.26 (s, 1H), 6.92 (d, 1H), 6.79 (br s, 1H), 4.00 (m, 2H), 3.60 (m, 2H). Mass (ES+)=345.3 (100%).

Workup

  1. custommicrowave irradiation
  2. concentrationThe reaction was concentrated to dryness and residue
  3. extractionthen extracted with methylene chloride
  4. dry with materialThe extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customSilica gel purification

Sources & evidence

ORD record
ord-d1a682657c994ac4be7c4adc3ee673b0
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

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