Dimethylformamide → HCID 136380450, compound

HRID 1294726Notes

Reaction equation

HRID 1294726 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[S:14])[NH:12][NH2:13])=[CH:6][CH:5]=1)([OH:3])=[O:2].[Br:15][C:16]1[C:17]([OH:25])=[C:18]([CH:21]=[C:22]([Br:24])[CH:23]=1)[CH:19]=O.CN(C)C=O.S(NN)(C1C=CC(C)=CC=1)(=O)=O>CS(C)=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[S:14])[NH:12][N:13]=[CH:19][C:18]2[CH:21]=[C:22]([Br:24])[CH:23]=[C:16]([Br:15])[C:17]=2[OH:25])=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 70243,5-DibromosalicylaldehydeHCID 15303P-ToluenesulfonylhydrazideHCID 27573784-(4-Carboxyphenyl)-3-thiosemicarbazide

Product 1

HCID 136380450HCID 136380450, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-(4-carboxyphenyl)-3-thiosemicarbazide (25 mg, 0.12 mmol) and 3,5-dibromo-2-hydroxybenzaldehyde (40 mg, 0.144 mmol) in dimethylsulfoxide (1 mL) was shaken with 4 Å molecular sieves for 18 h. Dimethylformamide (1 mL) was added, followed by PS-TsNHNH2 resin (80 mg, 0.230 mmol), shaking continued for 24 h, then the resin filtered off. The solution was chromatographed by reverse phase HPLC (CombiPrep ODS-A, 10–90% acetonitrile/water+0.1% trifluoroacetic acid) to give the title compound (24 mg, 42%) as a solid. MS (ES−) m/e 470, 472, 474 [M−H]−.

Workup

  1. filtrationthe resin filtered off
  2. customThe solution was chromatographed by reverse phase HPLC (CombiPrep ODS-A, 10–90% acetonitrile/water+0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-075aa30ca32c4db284198b22d8e8eee1
Source dataset
uspto-grants-2007_07
Patent number
US07241783B2

Reaction notes

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