Methyl iodide → 3-(5-Hexylsulfanyl-3H-imidazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine

HRID 1027568Notes

Reaction equation

HRID 1027568 reaction equation
[CH2:1]([S:7][C:8]1[N:12]=[CH:11][NH:10][C:9]=1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:19]SC1C(C2C=NC=CC=2)=NNC=1.CI>>[CH2:1]([S:7][C:8]1[N:12]=[CH:11][NH:10][C:9]=1[C:13]1[CH2:14][N:15]([CH3:19])[CH2:16][CH2:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 575480673-(5-Hexylsulfanyl-3H-imidazol-4-yl]-pyridineHCID 178503312HCID 178503312, compound

Product 1

HCID 252057153-(5-Hexylsulfanyl-3H-imidazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine

Procedure

3-(5-Hexylsulfanyl-3H-imidazol-4-yl]-pyridine (77) was converted to the title compound (76B) using the methodology described for the conversion of 21A to 22A (see Scheme 3) (the quarternization however was done at room temperature with a slight excess of CH3I). Yield: 70% (oil). LCMS (method A); Rt: 1.21 min, ([M+H]+=280). 1H-NMR (400 MHz, CDCl3): δ 7.53 (s, 1H), 6.40-6.29 (m, 1H), 3.45-3.41 (m, 2H), 2.79-2.72 (m, 2H), 2.59 (t, J=6 Hz, 2H), 2.45 (s, 3H), 2.41-2.37 (m, 2H), 1.55-1.49 (m, 2H), 1.38-1.31 (m, 2H), 1.30-1.19 (m, 4H), 0.85 (t, J=7 Hz, 3H).

Workup

  1. customhowever was done at room temperature

Sources & evidence

ORD record
ord-4de8007aeb0f44c6882e04357fd7f25d
Source dataset
uspto-grants-2014_05
Patent number
US08735388B2

Reaction notes

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