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

HRID 455102Notes

Reaction equation

HRID 455102 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.[S:21]1[CH:25]=[N:24][N:23]=[C:22]1[SH:26]>>[CH3:13][C:10]1[CH:11]=[CH:12][C:7]2[N:8]([C:4]([CH2:3][S:26][C:22]3[S:21][CH:25]=[N:24][N:23]=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 178527973HCID 178527973, compound

Product 1

HCID 670290026-Methyl-3-([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 1,3,4-thiadiazole-2-thiol. m/e+ 353 for C18H17N4S2 [M+H]+; 1H-NMR (300 MHz, CDCl3) δ 8.22 (d, J=10.2 Hz, 2H), 7.82 (dd, J=1.8, 6.3 Hz, 2H), 7.57 (d, J=9 Hz, 1H), 7.27 (d, J=9 Hz, 2H), 7.12 (dd, J=1.5, 9.0 Hz, 1H), 5.91 (s, 2H), 2.41 (s, 3H), 2.34 (s, 3H) ppm.

Sources & evidence

ORD record
ord-cf8316116ce84d6dac989c3d9904a1ff
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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