Pyridine → HCID 69892149, compound

HRID 48360Notes

Reaction equation

HRID 48360 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH:6]=[CH:7][C:8]1=[N:9][CH2:10][CH2:11][N:12]([CH3:20])[C:13]2[CH:18]=[CH:17][C:16](N)=[CH:15][C:14]1=2.[N:25]1C=CC=[CH:27][CH:26]=1.C(OC(=O)C)(=[O:33])C>ClCCl>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH:6]=[CH:7][C:8]1=[N:9][CH2:10][CH2:11][N:12]([CH3:20])[C:13]2[CH:18]=[CH:17][C:16]([CH2:27][C:26]([NH2:25])=[O:33])=[CH:15][C:14]1=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 69892163(E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-7-amine hydrochloride

Product 1

HCID 69892149HCID 69892149, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 43 mg, 0.125 mmol) of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-7-amine hydrochloride in 3 ml of dichloromethane was added 0.05 ml, 0.626 mmol) of pyridine, and 0.02 ml of acetic anhydride (0.15 mmol). The solution was stirred for 4 hours, concentrated under reduced pressure and the residue partitioned between brine and dichloromethane. The organic phase was dried over magnesium sulphate, filtered and evaporated, The residue was chromatographed on silica gel using first dichloromethane/methanol (98:2) and then dichloromethane/methanol (97:3) for the elution. The product was redissolved in a solution of hydrogen chloride in ethyl acetate and the solvent removed to afford (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-7-acetamide hydrochloride as a dark red solid MS: m/e 388.2 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue partitioned between brine and dichloromethane
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica gel using first dichloromethane/methanol (98:2)
  7. washdichloromethane/methanol (97:3) for the elution
  8. dissolutionThe product was redissolved in a solution of hydrogen chloride in ethyl acetate
  9. customthe solvent removed

Sources & evidence

ORD record
ord-89b9773979c04cc3b962b4ac3aef8521
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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