Triethylamine → HCID 22405326, compound

HRID 440781Notes

Reaction equation

HRID 440781 reaction equation
N1[N:10]2[C:4](=[CH: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.[CH2:15](N(CC)CC)C.S(Cl)(Cl)=O.[CH3:26][C:27]1[CH:42]=[CH:41][C:30]([O:31][C:32]2[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=2)=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:26][C:27]1[CH:42]=[CH:41][C:30]([O:31][C:32]2[CH:40]=[CH:39][C:35]([C:36]([N:6]3[C:7]4[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=4[CH2:9][N:10]4[CH:15]=[CH:2][CH:3]=[C:4]4[CH2:5]3)=[O:37])=[CH:34][CH:33]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 17879037HCID 17879037, compound2×HCID 22605451HCID 22605451, compound

Product 1

HCID 22405326HCID 22405326, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.0 g of 10,11-dihydro-5H-pyrazolo[5,1-c][1,4]benzodiazepine in 30 ml of methylene chloride, under nitrogen, while cooling to 0° C. is added dropwise 30 ml of triethylamine followed by a solution of 1.2 equivalents of 4-(4-methylphenoxy)benzoyl chloride in 10 ml of CH2Cl2 (Reference Example 53) prepared from Reference Example 52 and thionyl chloride. The reactants are stirred at room temperature for 16 hours and concentrated in vacuo to a residue. The residue is dissolved in methylene chloride, washed with water, 2N HCl, water, saturated aqueous NaHCO3, water and dried (MgSO4) and evaporated in vacuo to give 2.2 g of the desired product. MS(M+H=395.1)

Workup

  1. concentrationconcentrated in vacuo to a residue
  2. dissolutionThe residue is dissolved in methylene chloride
  3. washwashed with water, 2N HCl, water, saturated aqueous NaHCO3, water
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-162049e6b9f54d7cb2bc0ad0e0c65418
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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