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

HRID 2043071Notes

Reaction equation

HRID 2043071 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 quaternization 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-f6245f958a074998a562aa371113e0c7
Source dataset
uspto-grants-2013_11
Patent number
US08586606B2

Reaction notes

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