Bromomethyl 4-methoxyphenyl ketone → 2-(4-(3-(4-Chlorophenyl)-1,2,4-thiadiazol-5-yl)piperazin-1-yl)-1-(4-methoxyphenyl)ethanone

HRID 570567Notes

Reaction equation

HRID 570567 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[S:10][N:9]=2)=[CH:4][CH:3]=1.Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:22].CCN(C(C)C)C(C)C>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][N:16]([CH2:20][C:21]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)=[O:22])[CH2:15][CH2:14]3)[S:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketone2×HCID 81531DiisopropylethylamineHCID 577122563-(4-Chlorophenyl)-5-(piperazin-1-yl)-1,2,4-thiadiazole

Product 1

HCID 711862252-(4-(3-(4-Chlorophenyl)-1,2,4-thiadiazol-5-yl)piperazin-1-yl)-1-(4-methoxyphenyl)ethanoneYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(4-chlorophenyl)-5-(piperazin-1-yl)-1,2,4-thiadiazole (539 mg, 1.92 mmol), 2-bromo-4′-methoxyacetophenone (440 mg, 1.92 mmol) and DIPEA (744 mg, 1.01 ml, 5.76 mmol) in 10 mL EtOH was stirred for 2 h at RT. Another portion 2-bromo-4′-methoxyacetophenone (220 mg, 960 μmol) was added and stirring continued for 2 h. The reaction was filtered off and washed with MeOH (4×5 mL) and Et2O (2×5 mL). The filter cake was dried in vacuo at 50° C. to yield 526 mg (64%) of the title compound as white solid. MS (m/e): 429.2 (MH+).

Workup

  1. stirringstirring
  2. waitcontinued for 2 h
  3. filtrationThe reaction was filtered off
  4. washwashed with MeOH (4×5 mL) and Et2O (2×5 mL)
  5. customThe filter cake was dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-fd83e1c911264bb9816145be66626ffc
Source dataset
uspto-grants-2015_05
Patent number
US09023852B2

Reaction notes

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