Water → HCID 135759121, compound

HRID 1153856Notes

Reaction equation

HRID 1153856 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3=[N:12][N:13]([CH3:15])[CH:14]=[C:9]3[C:8]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[N:7][C:6]=2[CH:22]=1.Br[CH2:24][CH:25]1[CH2:27][CH2:26]1.C(N(CC)CC)C.O>C(#N)C>[CH:25]1([CH2:24][N:19]2[CH2:20][CH2:21][N:16]([C:8]3[C:9]4[C:10](=[N:12][N:13]([CH3:15])[CH:14]=4)[NH:11][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:22][C:6]=4[N:7]=3)[CH2:17][CH2:18]2)[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 81503BromomethylcyclopropaneHCID 135759115HCID 135759115, compound

Product 1

HCID 135759121HCID 135759121, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 7-fluoro-2,10-dihydro-2-methyl-4-(1-piperazinyl)pyrazolo[3,4-b][1,5]benzodiazepine (1.0 g), bromomethylcyclopropane (0.5 g) and triethylamine (0.0375 g) in acetonitrile (30 ml) was stirred at ambient temperature for 20 hours. The solution was poured into water and the product extracted with chloroform (3×). The organic extract was washed with saturated brine and water, dried over magnesium sulphate, the solvent removed and the residue crystallised from ethyl acetate to give the title compound m.p. 188°-189° C. 4-(4-Benzyl-1-piperazinyl)-7-fluoro-2,10-dihydro-2-methyl-pyrazolo[3,4-b][1,5]benzodiazepine was similarly prepared, m.p. 241°-245° C. (ethyl acetate-diethyl ether).

Workup

  1. extractionthe product extracted with chloroform (3×)
  2. extractionThe organic extract
  3. washwas washed with saturated brine and water
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed
  6. customthe residue crystallised from ethyl acetate

Sources & evidence

ORD record
ord-c9cd878b30e34440a69a3b181e0fc89d
Source dataset
uspto-grants-1984_12
Patent number
US04486591

Reaction notes

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