Propylamine → HCID 67946701, compound

HRID 1164826Notes

Reaction equation

HRID 1164826 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14][CH:15]=[CH:16][OH:17])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=[C:10]([CH:21]([CH3:23])[CH3:22])[C:9]=2[C:24]([OH:26])=O)=[CH:4][CH:3]=1.O[N:28]1[C:32]2C=CC=[CH:36][C:31]=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1.C(N)CC>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([CH2:14][CH:15]=[CH:16][OH:17])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=[C:10]([CH:21]([CH3:22])[CH3:23])[C:9]=2[C:24]([NH:28][CH2:32][CH2:31][CH3:36])=[O:26])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7852PropylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 67946621HCID 67946621, compound

Product 1

HCID 67946701HCID 67946701, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 4-(4-fluorophenyl)-5-(3-hydroxy-2-propenyl)-2,6-bis(1-methylethyl)-3-pyridinecarboxylic acid (4.0 g, 0.0112 mol) was added 1.51 g of 1-hydroxybenzotriazole (0.0112 mol) followed by 2.31 g of DCC (0.0112 mol). The resulting mixture was stirred 25 minutes, then 1.84 ml of n-propylamine (0.0224 mol) was added. The resulting mixture was stirred for 72 hrs and then was taken up in ethyl acetate (500 ml), filtered, washed with water (2×250 ml), washed with 30% saturated NaHCO3 (1×150 ml), washed with brine (1×150 ml), dried (MgSO4), concentrated under reduced pressure, and chromatographed on silica (1:1 hexane:ethyl acetate) to yield 1.65 g of the title compound.

Workup

  1. stirringThe resulting mixture was stirred for 72 hrs
  2. filtrationfiltered
  3. washwashed with water (2×250 ml)
  4. washwashed with 30% saturated NaHCO3 (1×150 ml)
  5. washwashed with brine (1×150 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customchromatographed on silica (1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-564aae1db68348ceb8f0e1ff06ded6a1
Source dataset
uspto-grants-1990_03
Patent number
US04906624

Reaction notes

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