2-Chloronicotinoyl chloride → HCID 86623756, compound

HRID 448080Notes

Reaction equation

HRID 448080 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:14][C:15]1[N:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18]>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:17]([C:16]1[C:15]([Cl:14])=[N:23][CH:22]=[CH:21][CH:20]=1)=[O:18])[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 27745412-Chloronicotinoyl chlorideHCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

Product 1

HCID 86623756HCID 86623756, 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 2-chloronicotinoyl chloride (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 0.91 (t, 3 H) 1.31-1.39 (m, 2 H) 1.58-1.67 (m, 2 H) 2.19 (s, 3 H) 2.21 (s, 3 H) 3.93-3.98 (m, 2 H) 6.15 (s, 1 H) 7.47 (dd, 1 H) 7.94 (dd, 1 H) 8.41 (dd, 1 H); MS (ESI) m/z 323 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-c2392ac459c748f384156421a8d804aa
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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