Triethylamine → 1,2-Dihydro-8-(dimethylamino)methylbenzo[b]pyrrolo[3,2,1-jk][1,2,4]triazolo[4,3-d][1,4]benzodiazepine

HRID 703432Notes

Reaction equation

HRID 703432 reaction equation
[CH2:1]1[N:12]2[C:13]3[C:3](=[CH:4][CH:5]=[CH:6][C:7]=3[C:8](=S)[NH:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=32)[CH2:2]1.Cl.CN(C[C:24]([NH:26][NH2:27])=O)C.[CH2:28]([N:30]([CH2:33]C)[CH2:31]C)C>CN(C)C=O>[CH3:28][N:30]([CH2:33][C:15]1[CH:16]=[CH:17][C:10]2[N:9]3[CH:24]=[N:26][N:27]=[C:8]3[C:7]3[CH2:6][CH2:5][CH:4]=[C:3]4[CH:2]=[CH:1][N:12]([C:13]=34)[C:11]=2[CH:14]=1)[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68318N,N-Dimethylglycine hydrazide hydrochlorideHCID 15132539HCID 15132539, compound

Product 1

HCID 679230661,2-Dihydro-8-(dimethylamino)methylbenzo[b]pyrrolo[3,2,1-jk][1,2,4]triazolo[4,3-d][1,4]benzodiazepineYield 47.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-Dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-thione (4 g) was added to a solution of dimethylaminoacetic hydrazide hydrochloride (2 g) and triethylamine (2.4 ml) in dimethylformamide (25 ml). The mixture was refluxed overnight, cooled, and concentrated under reduced pressure. The residue was purified by high performance liquid chromatography (2.5% methanol/dichloromethane). The appropriate fractions were triturated with dry ether to yield 2.4 g (47.2%) of product, mp 164°-165° C.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by high performance liquid chromatography (2.5% methanol/dichloromethane)
  5. customThe appropriate fractions were triturated with dry ether

Sources & evidence

ORD record
ord-67992894610346ea9c9771049ff109f5
Source dataset
uspto-grants-1991_01
Patent number
US04983601

Reaction notes

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