3-(Chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride → 6-Methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-2-p-tolyl-imidazo[1,2-a]pyridine

HRID 455101Notes

Reaction equation

HRID 455101 reaction equation
Cl.Cl[CH2:3][C:4]1[N:8]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]2=[N:6][C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1.[CH3:21][C:22]1[S:26][C:25]([SH:27])=[N:24][N:23]=1>>[CH3:13][C:10]1[CH:11]=[CH:12][C:7]2[N:8]([C:4]([CH2:3][S:27][C:25]3[S:26][C:22]([CH3:21])=[N:23][N:24]=3)=[C:5]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[N:6]=2)[CH:9]=1

Participants

3

Reactant 2

HCID 670287243-(Chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochlorideHCID 178434161HCID 178434161, compound

Product 1

HCID 670277706-Methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-2-p-tolyl-imidazo[1,2-a]pyridine

Procedure

The title compound was prepared according to Method A and the experimentals described for compound 139 from 3-(chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride and 5-methyl-1,3,4-thiadiazole-2-thiol. m/e− 367 for C19H19N4S2 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.86 (d, J=8.0 Hz, 2H), 7.55 (d, J=9.1 Hz, 1H), 7.28 (d, J=8.0 Hz, 2H), 7.09 (dd, J=1.4, 9.1 Hz, 1H), 5.83 (s, 2H), 2.40 (s, 3H), 2.37 (s, 3H), 2.33 (s, 3H) ppm; 13C-NMR (100 MHz, CDCl3, δ) 186.983, 156.637, 146.840, 144.588, 138.165, 131.265, 129.597, 128.800, 128.649, 122.931, 122.787, 116.971, 113.923, 44.131, 21.557, 18.638, 16.606 ppm.

Sources & evidence

ORD record
ord-e7374ba333ae4405acfa3eb8f057870d
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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