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

HRID 2050999Notes

Reaction equation

HRID 2050999 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]benzodiazepin6-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% methano/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% methano/dichloromethane)
  5. customThe appropriate fractions were triturated with dry ether

Sources & evidence

ORD record
ord-261a1c550af5459ba45f8471822a41d2
Source dataset
uspto-grants-1991_05
Patent number
US05015738

Reaction notes

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