Diisopropylcarbodiimide → 4-(2-[4-(4-Methyl-4-(methyldisulphanyl)pentanoyl)piperazin-1-yl]ethoxy)-2,6-bis(hydroxymethyl)pyridine

HRID 446650Notes

Reaction equation

HRID 446650 reaction equation
[CH3:1][C:2]([S:9][S:10][CH3:11])([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=O.C(N=C=NC(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.[N:32]1([CH2:38][CH2:39][O:40][C:41]2[CH:46]=[C:45]([CH2:47][OH:48])[N:44]=[C:43]([CH2:49][OH:50])[CH:42]=2)[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>CN(C=O)C>[CH3:8][C:2]([S:9][S:10][CH3:11])([CH3:1])[CH2:3][CH2:4][C:5]([N:35]1[CH2:36][CH2:37][N:32]([CH2:38][CH2:39][O:40][C:41]2[CH:46]=[C:45]([CH2:47][OH:48])[N:44]=[C:43]([CH2:49][OH:50])[CH:42]=2)[CH2:33][CH2:34]1)=[O:7]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 115646344-Methyl-4-(methyldisulfanyl)pentanoic acidHCID 670322814-[2-(Piperazin-1-yl)ethoxy]-2,6-bis(hydroxymethyl)pyridine

Product 1

HCID 866712934-(2-[4-(4-Methyl-4-(methyldisulphanyl)pentanoyl)piperazin-1-yl]ethoxy)-2,6-bis(hydroxymethyl)pyridineYield 39.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

344 μL of TEA and then, after stirring for 10 min, 748 mg of 4-methyl-4-(methyldisulphanyl)pentanoic acid, 417 μl of diisopropylcarbodiimide and 69 mg of 1-hydroxybenzotriazole hydrate are added to 600 mg of 4-[2-(piperazin-1-yl)ethoxy]-2,6-bis(hydroxymethyl)pyridine in solution in 12 ml of DMF. After 15 h at AT, the mixture is concentrated under RP, 15 ml of water are added and extraction is carried out 2× with AcOEt. The combined organic phases are dried over MgSO4 and concentrated under RP, and the residue is purified by flash chromatography on silica (Analogix Super Flash SiO2 SF25-80 g) using a gradient from 2 to 10% of MeOH in DCM. 390 mg of 4-(2-[4-(4-methyl-4-(methyldisulphanyl)pentanoyl)piperazin-1-yl]ethoxy)-2,6-bis(hydroxymethyl)pyridine are thus obtained.

Workup

  1. concentrationthe mixture is concentrated under RP, 15 ml of water
  2. additionare added
  3. extractionextraction
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. concentrationconcentrated under RP
  6. customthe residue is purified by flash chromatography on silica (Analogix Super Flash SiO2 SF25-80 g)

Sources & evidence

ORD record
ord-3060a534d5e1498a84c488e918232247
Source dataset
uspto-grants-2013_07
Patent number
US08481042B2

Reaction notes

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