Pyridine → HCID 22903480, compound

HRID 1440275Notes

Reaction equation

HRID 1440275 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:32])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:31])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29][OH:30])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:33]=1.N1C=CC=CC=1.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:32])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:31])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29][O:30][S:41]([CH3:40])(=[O:43])=[O:42])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:33]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 22903479HCID 22903479, compound

Product 1

HCID 22903480HCID 22903480, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 7-chloro-1-{6-[2-(2-hydroxyethoxy)benzoylamino]-nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.5 g )in pyridine (10 ml) is added with stirring methanesulfonyl chloride (0.1 ml) under ice-cooling, and the mixture is stirred at room temperature for 2 hours. To the reaction solution is added water, and the precipitated crystals are collected by filtration, and dissolved in dichloromethane. The mixture is washed successively with diluted hydrochloric acid and water, dried over magnesium sulfate and evaporated under reduced pressure. The residue is crystallized from diethyl ether to give 7-chloro-1-{6-[2-(2-methanesulfonyloxyethoxy)benzoylamino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.59 g) as white powder.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated crystals are collected by filtration
  3. dissolutiondissolved in dichloromethane
  4. washThe mixture is washed successively with diluted hydrochloric acid and water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-f3f3620df9f6467587fbc5fbf01a007c
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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