Diisopropylethylamine → 3-(Chloromethyl)-N-[(2,4-dimethoxyphenyl)methyl]-1,2,4-thiadiazol-5-amine

HRID 1685084Notes

Reaction equation

HRID 1685084 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([CH2:7][Cl:8])[N:3]=1.CCN(C(C)C)C(C)C.[CH3:18][O:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:21]=1[CH2:22][NH2:23]>C(Cl)Cl>[Cl:8][CH2:7][C:4]1[N:3]=[C:2]([NH:23][CH2:22][C:21]2[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:20]=2[O:19][CH3:18])[S:6][N:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3326105-Chloro-3-(chloromethyl)-1,2,4-thiadiazoleHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 580550883-(Chloromethyl)-N-[(2,4-dimethoxyphenyl)methyl]-1,2,4-thiadiazol-5-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chloro-3-chloromethyl-[1,2,4]thiadiazole (3 g, 18 mmol, [74461-64-6]) in DCM (20 mL) was treated with DIPEA (1 eq), followed by 2,4-dimethoxybenzylamine (1 eq). After stirring overnight, the mixture was concentrated and purified by silica gel chromatography (10% MeOH/EtOAc) to afford (3-chloromethyl-[1,2,4]thiadiazol-5-yl)-(2,4-dimethoxy-benzyl)-amine, which was used directly in the next step.

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by silica gel chromatography (10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-730e7d7044b44ed5898ce01385d84508
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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