3-(Chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride → 3-Methylsulfanyl-4-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-4H-[1,2,4]thiadiazole-5-thione

HRID 455071Notes

Reaction equation

HRID 455071 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][S:22][C:23]1[NH:27][C:26](=[S:28])[S:25][N:24]=1>>[CH3:21][S:22][C:23]1[N:27]([CH2:3][C:4]2[N:8]3[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]3=[N:6][C:5]=2[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:26](=[S:28])[S:25][N:24]=1

Participants

3

Reactant 2

HCID 670287243-(Chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochlorideHCID 178503623HCID 178503623, compound

Product 1

HCID 866551173-Methylsulfanyl-4-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-4H-[1,2,4]thiadiazole-5-thione

Procedure

The title compound was prepared according to Method A and the experimentals described for compound 92 from 3-(chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride and 3-(methylthio)-1,2,4-thiadiazole-5(4H)-thione. m/e+ 399 for C19H19N4S3 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 7.96 (s, 1H), 7.67 (d, J=7.7 Hz, 2H), 7.57 (d, J=9.1 Hz, 1H), 7.27 (d, J=8.0 Hz, 2H), 7.11 (d, J=9.1 Hz, 1H), 5.04 (s, 2H), 2.67 (s, 3H), 2.39 (s, 3H), 2.36 (s, 3H) ppm; 13C-NMR (100 MHz, CDCl3, δ) 186.346, 171.423, 145.801, 144.701, 138.203, 130.870, 129.680, 128.573, 128.300, 122.825, 121.733, 117.047, 111.982, 29.739, 21.444, 18.577, 14.968, ppm.

Sources & evidence

ORD record
ord-44446d89143d47569a22ad7f51e879ff
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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