2-Dimethylaminopyridine → HCID 14304997, compound

HRID 477057Notes

Reaction equation

HRID 477057 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[CH2:9][CH2:8]1.[O:18]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:21](=[O:22])[C:20]([C:29](O)=[O:30])=[C:19]1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CN(C1C=CC=CN=1)C.CS(Cl)(=O)=O>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:29]([C:20]2[C:21](=[O:22])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:18][C:19]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:30])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 12674946HCID 12674946, compoundHCID 14295622HCID 14295622, compound

Product 1

HCID 14304997HCID 14304997, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.6 g of the 4-[4-(2-pyridyl)-piperazin-1-yl]butylamine obtained above were added to a reaction mixture cooled to -2020 C. which contained, in 100 ml of absolute dichloromethane, a mixed anhydride produced in a manner analogous to Example 1 (a) from 4.0 g flavone-3-carboxylic acid, 3.367 g dimethylaminopyridine and 1.28 ml methanesulfonyl chloride. The reaction mixture was allowed to warm up to room temperature and stirred at room temperature for two hours. Subsequently the reaction mixture was worked up analogously to Example 3, and the resulting title compound was recrystallized from ethylacetate. There were obtained 4.7 g 3-{4-[4-(2-pyridyl)-piperazin-1-yl]-butylaminocarbonyl}flavone.

Workup

  1. additionabove were added to a reaction mixture
  2. temperaturecooled to -2020 C
  3. customthe resulting title compound was recrystallized from ethylacetate

Sources & evidence

ORD record
ord-9ada4ac23ead42588bc52fa437a22f17
Source dataset
uspto-grants-1989_12
Patent number
US04886806

Reaction notes

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