2,5-Dichloropyridine-3-carbonitrile → HCID 67400202, compound

HRID 914419Notes

Reaction equation

HRID 914419 reaction equation
C([O:5][C:6](=[O:19])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][NH2:18])[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.[Cl:20][C:21]1[N:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:22]=1[C:23]#[N:24].Cl.O1[CH2:36][CH2:35]OCC1>O1CCOCC1>[ClH:20].[Cl:29][C:26]1[CH:25]=[C:22]([C:23]#[N:24])[C:21]([N:18]([CH2:21][CH2:22][CH2:25][CH2:26][CH2:27][CH2:35][CH3:36])[CH2:17][CH2:16][C:14]2[N:15]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:5])=[O:19])[S:12][CH:13]=2)=[N:28][CH:27]=1

Participants

5

Reactant 3

HCID 142116462,5-Dichloropyridine-3-carbonitrileHCID 204431481,4-Dioxane hydrochlorideHCID 597594492-{[4-(2-Aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 67400202HCID 67400202, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A compound obtained by using, as starting materials, 2-{[4-(2-aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester synthesized in Example 7 and 2,5-dichloronicotinonitrile synthesized in reference to non-patent reference [Liebigs Ann. Chem., 487, 127 (1931)] and the like, and by operations similar to those of Example 265-1 and Example 265-2, was dissolved in dioxane, an excess amount of 4 mol/L hydrochloric acid-dioxane was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=10:1) to give the title compound as a colorless oil.

Workup

  1. customA compound obtained
  2. customsynthesized in reference to non-patent reference [Liebigs Ann. Chem., 487, 127 (1931)]
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-455b3f06048042738c27446d6303b276
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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