Diisopropylethylamine → HCID 59408735, compound

HRID 1188104Notes

Reaction equation

HRID 1188104 reaction equation
[I-].ClC1C=CC=C[N+]=1C.CCN(C(C)C)C(C)C.[C:19]1([CH3:31])[CH:24]=[CH:23][C:22]([C:25]2[S:29][C:28]([NH2:30])=[N:27][CH:26]=2)=[CH:21][CH:20]=1.[Br:32][C:33]1[S:34][C:35]([C:38](O)=[O:39])=[CH:36][N:37]=1>CN(C=O)C.CCOC(C)=O>[Br:32][C:33]1[S:34][C:35]([C:38]([NH:30][C:28]2[S:29][C:25]([C:22]3[CH:21]=[CH:20][C:19]([CH3:31])=[CH:24][CH:23]=3)=[CH:26][N:27]=2)=[O:39])=[CH:36][N:37]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 9607605-(4-Methylphenyl)-1,3-thiazol-2-amineHCID 27632102-Bromothiazole-5-carboxylic acid

Product 1

HCID 59408735HCID 59408735, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-methylpyridinium iodide (0.55 g, 2.2 mmol), DIEA (0.37 g, 2.9 mmol) and 5-p-tolylthiazol-2-amine (0.27 g, 1.44 mmol) were added to a suspension of 2-bromothiazole-5-carboxylic acid (0.30 g, 1.44 mmol) in DMF (5 mL). The resulting solution was stirred at RT till completion of the reaction. The mixture was then diluted with AcOEt, washed with water, dried with Na2SO4 and concentrated. The crude product was purified by column (30% AcOEt/PE), yielding 2-bromo-N-(5-p-tolylthiazol-2-yl)thiazole-5-carboxamide (250 mg, 46%) as a solid.

Workup

  1. washwashed with water
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column (30% AcOEt/PE)

Sources & evidence

ORD record
ord-47c96296d7324b9c8dab4ccceab79b82
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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