Methanesulfonyl chloride → HCID 14304999, compound

HRID 2050680Notes

Reaction equation

HRID 2050680 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:19])[C:15]=1[C:16]([OH:18])=O)=[CH:12][CH:11]=[CH:10][CH:9]=2.S(Cl)(C)(=O)=O.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:19])[C:15]=1[C:16]([N:41]1[CH2:42][CH2:43][N:38]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=3)[CH2:39][CH2:40]1)=[O:18])=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 944591-(2-Pyridyl)piperazineHCID 143049774-Oxo-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-3-carboxylic acid

Product 1

HCID 14304999HCID 14304999, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

8 g of 3',4',5'-trimethoxy-flavone-3-carboxylic acid with 5.5 g 4-dimethylaminopyridine and 2.2 ml mesylchloride in 100 ml absolute dichloromethane were converted into the mixed anhydride analogously to Example 1 (a), and this was then reacted with 3.6 g 1-(2-pyridyl)-piperazine analogously to Example 1 (b). The working up of the reaction mixture and the purification of the crude title compound obtained were carried out analogously to Example 1 (b). 7.5 g of 3',4',5'-trimethoxy-3-{[4-(2-pyridyl)-piperazin-1-yl]-carbonyl} flavone were obtained.

Workup

  1. customThe working up of the reaction mixture and the purification of the crude title compound
  2. customobtained

Sources & evidence

ORD record
ord-c091c7c01c424678bb01e216726657f9
Source dataset
uspto-grants-1991_05
Patent number
US05013852

Reaction notes

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