5-Chloro-3-(chloromethyl)-1,2,4-thiadiazole → HCID 9880085, compound

HRID 1796011Notes

Reaction equation

HRID 1796011 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([CH2:7][Cl:8])[N:3]=1.C([Sn](CCCC)(CCCC)[C:14]1[N:18]2[CH:19]=[CH:20][C:21]([C:23]([F:26])([F:25])[F:24])=[N:22][C:17]2=[N:16][CH:15]=1)CCC>>[Cl:8][CH2:7][C:4]1[N:3]=[C:2]([C:14]2[N:18]3[CH:19]=[CH:20][C:21]([C:23]([F:24])([F:25])[F:26])=[N:22][C:17]3=[N:16][CH:15]=2)[S:6][N:5]=1

Participants

3

Reactant 2

HCID 3326105-Chloro-3-(chloromethyl)-1,2,4-thiadiazoleHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 9880085HCID 9880085, compoundYield 25.7%

Procedure

5-Chloro-3-chloromethyl-[1,2,4]thiadiazole (360 mg, 2.13 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.4 mmol) by the method of Example 1 to afford 3-(3-chloromethyl-[1,2,4]thiadiazol-5-yl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (115 mg) as a yellow solid: δH (400 MHz, DMSO) 5.08 (2H, s), 7.94 (1H, d, J 7), 9.12 (1H, s), 10.03 (1H, d, J 7); m/z (ES+) 320 (M++H).

Sources & evidence

ORD record
ord-a508942ec5b54a3fa4b00e97193e5463
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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