Pyridine → HCID 69892149, compound

HRID 48361Notes

Reaction equation

HRID 48361 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.CS(Cl)(=O)=[O:33]>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 31297Methanesulfonyl chlorideHCID 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 100 mg, 0.219 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 0.073 ml, 0.9 mmol) of pyridine, and 0.018 ml, (0.231 mmol) of methanesulphonyl chloride. The solution was stirred for 1 hour, 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. There was obtained (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-7-acetamide hydrochloride as a brown solid MS: m/e 424.1 [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

Sources & evidence

ORD record
ord-4dc794fc09b944e3bc204fbc98b2b5c2
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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