3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 69166888, compound

HRID 448078Notes

Reaction equation

HRID 448078 reaction equation
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:7]=1[CH3:13])[CH2:3][CH2:4][CH3:5].Cl.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1>CN(C1C=CN=CC=1)C>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:15]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:22])[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

Product 1

HCID 69166888HCID 69166888, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a 20 mL vial 3-butyl-2,4,5-trimethylthiazol-3-ium iodide (48 mg in 0.5 mL DMA, 0.16 mmol, 1 equiv.) was added, followed by TEA (38 mg in 0.5 mL DMA, 0.37 mmol, 2.4 equiv.) and the solution went black. DMAP (2 mg in 0.5 mL DMA, 0.016 mmol, 0.1 equiv) was added next, followed by nicotinoyl chloride hydrochloride (0.9 mL of 0.2M in DMA, 1.2 equiv). The mixture was shaken overnight at room temperature and then concentrated in vacuo. The resulting residue was taken up in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.94 (t, 3 H) 1.36-1.46 (m, 2 H) 1.61-1.68 (m, 2 H) 2.19 (s, 3 H) 2.22 (s, 3 H) 4.07-4.12 (m, 2 H) 6.69 (s, 1 H) 7.68-7.78 (m, 1 H) 8.54-8.61 (m, 1 H) 8.72-8.80 (m, 1 H) 9.18-9.29 (m, 1 H); MS (ESI) m/z 289 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-4228edca180a430db51b6f08ed8a8a0a
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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