Nicotinic Acid → HCID 10743384, compound

HRID 1275548Notes

Reaction equation

HRID 1275548 reaction equation
[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:24]2[C:12](=[C:13]([CH3:27])[C:14]3[N:15]([CH3:26])[C:16]4[CH:17]=[CH:18][C:19]([OH:25])=[CH:20][C:21]=4[C:22]=3[CH:23]=2)[CH:11]=[CH:10][N:9]=1)=[O:7].[C:29](O)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1.C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:24]2[C:12](=[C:13]([CH3:27])[C:14]3[N:15]([CH3:26])[C:16]4[CH:17]=[CH:18][C:19]([O:25][C:29]([C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)=[O:36])=[CH:20][C:21]=4[C:22]=3[CH:23]=2)[CH:11]=[CH:10][N:9]=1)=[O:7]

Participants

6

Reactant 4

HCID 938Nicotinic Acid2×HCID 10868Dicyclohexylcarbodiimide2×HCID 218852-DimethylaminopyridineHCID 177330156055-46-8

Product 1

HCID 10743384HCID 10743384, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture containing 3 g of 1-[(2-dimethylaminoethyl)aminocarbonyl]-5,6-dimethyl-9-hydroxy-6H-pyrido[4,3-b]carbazole, 1.5 g of nicotinic acid, 3.7 g of dicyclohexylcarbodiimide and 1.5 g of dimethylaminopyridine dissolved in 100 ml of pyridine is stirred at room temperature for 16 hours. At the end of 16 hours, a further 2 g of dicyclohexylcarbodiimide and 0.75 g of nicotinic acid are added and the mixture is stirred for a further 24 hours and concentrated to dryness. The residue is taken up in dichloromethane and washed with sodium hydrogen carbonate, and the dichloromethane phase is concentrated to remove by filtration as much as possible of the dicyclohexylurea formed, and the filtrate is concentrated to dryness. The residue is chromatographed on silica using a mixture of toluene, ethanol and triethylamine (100:10:05) as eluant. 3.5 g of the desired product are obtained, m.p. (cap): 190-192° C.

Workup

  1. stirringthe mixture is stirred for a further 24 hours
  2. concentrationconcentrated to dryness
  3. washwashed with sodium hydrogen carbonate
  4. concentrationthe dichloromethane phase is concentrated
  5. customto remove by filtration as much as possible of the dicyclohexylurea
  6. customformed
  7. concentrationthe filtrate is concentrated to dryness
  8. customThe residue is chromatographed on silica using
  9. additiona mixture of toluene, ethanol and triethylamine (100:10:05) as eluant

Sources & evidence

ORD record
ord-805ae472a2ac4f91b49ed0f84d65c204
Source dataset
uspto-grants-2000_12
Patent number
US06162811

Reaction notes

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