Triethylamine → HCID 22405328, compound

HRID 1956342Notes

Reaction equation

HRID 1956342 reaction equation
[N:1]1[N:10]2[C:4]([CH2:5][NH:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:22]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=[CH:26][C:25]([C:28](Cl)=[O:29])=[CH:24][CH:23]=1>C(Cl)Cl>[C:22]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:23]=[CH:24][C:25]([C:28]([N:6]2[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][N:10]3[N:1]=[CH:2][CH:3]=[C:4]3[CH2:5]2)=[O:29])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 130628255,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine

Product 1

HCID 22405328HCID 22405328, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 185 mg of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine in 50 ml of methylene chloride containing 2.0 ml of triethylamine is slowly added a solution of 300 mg of 4-biphenylcarbonyl chloride in 10 ml of methylene chloride at room temperature. The reaction mixture is stirred at room temperature for 16 hours and evaporated in vacuo to give a residue. The residue is extracted with chloroform, washed with water, dried over Na2 SO4, filtered and the filtrate evaporated in vacuo to give a residue which is purified by column chromatography on silica gel by elution with 30% ethyl acetate-hexane to give 250 mg of the desired product as a solid. Mass spectrum: M+H:366.

Workup

  1. customevaporated in vacuo
  2. customto give a residue
  3. extractionThe residue is extracted with chloroform
  4. washwashed with water
  5. customdried over Na2 SO4
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customto give a residue which
  9. customis purified by column chromatography on silica gel by elution with 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-a4a36ac6275440da9f6778564bc3ffb5
Source dataset
uspto-grants-1998_07
Patent number
US05780471

Reaction notes

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