Diisopropylethylamine → 2-{2-[5-(4-chloro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-N-methyl-acetamide

HRID 1046932Notes

Reaction equation

HRID 1046932 reaction equation
[CH:1]([C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][CH2:6][C:7]([NH:9][CH3:10])=[O:8])=O.[Cl:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([NH:22][NH2:23])=[S:21])=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C.[F:35][C:36]1[CH:44]=[C:43]([F:45])[CH:42]=[C:41]([F:46])[C:37]=1[C:38](Cl)=[O:39]>C(Cl)Cl>[Cl:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]2[S:21][CH:1]([C:3]3[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=3[O:5][CH2:6][C:7]([NH:9][CH3:10])=[O:8])[N:23]([C:38](=[O:39])[C:37]3[C:41]([F:46])=[CH:42][C:43]([F:45])=[CH:44][C:36]=3[F:35])[N:22]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 124770754-Chloro-thiobenzoic acid hydrazideHCID 28561351Acetamide, 2-(2-formylphenoxy)-N-methyl-

Product 1

HCID 580257372-{2-[5-(4-chloro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-N-methyl-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 2-(2-formyl-phenoxy)-N-methyl-acetamide (0.0311 mmol) is added to 4-chloro-thiobenzoic acid hydrazide (0.0342 mmol) in 0.1 mL of CH2Cl2. After 10 minutes, DIEA (0.05 mL) and 2,4,6-trifluoro-benzoyl chloride (0.0467 mmol) are added. The mixture is kept at room temperature overnight. After removal of solvent, the residue is purified by preparative HPLC (20-100% MeCN/H2O gradient) to give the product 2-{2-[5-(4-chloro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-N-methyl-acetamide as an off white solid: LC/MS (ES+): 520.1 (M+1)+.

Workup

  1. waitThe mixture is kept at room temperature overnight
  2. customAfter removal of solvent
  3. customthe residue is purified by preparative HPLC (20-100% MeCN/H2O gradient)

Sources & evidence

ORD record
ord-6bf32721502742af8949b2e70460a392
Source dataset
uspto-grants-2013_10
Patent number
US08569345B2

Reaction notes

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