Diisopropylethylamine → HCID 59408750, compound

HRID 1188108Notes

Reaction equation

HRID 1188108 reaction equation
[I-].ClC1C=CC=C[N+]=1C.CCN(C(C)C)C(C)C.[NH2:19][C:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[N:22]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[N:21]=1.[Br:39][C:40]1[S:41][C:42]([C:45](O)=[O:46])=[CH:43][N:44]=1>CN(C=O)C.CCOC(C)=O>[Br:39][C:40]1[S:41][C:42]([C:45]([NH:19][C:20]2[CH:24]=[C:23]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[N:22]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[N:21]=2)=[O:46])=[CH:43][N:44]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 27632102-Bromothiazole-5-carboxylic acidHCID 59408733HCID 59408733, compound

Product 1

HCID 59408750HCID 59408750, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-methylpyridinium iodide (0.84 g, 3.3 mmol), DIPEA (0.78 mL, 4.4 mmol) and tert-butyl 3-amino-5-(4-fluorophenyl)-1H-pyrazole-1-carboxylate (0.5 g, 2.2 mmol) were added to a solution of 2-bromothiazole-5-carboxylic acid (0.45 g, 2.2 mmol) in DMF (6 mL). The resulting solution was stirred at RT till completion of the reaction. Then the mixture was diluted with AcOEt, washed with water, dried with Na2SO4 and concentrated. The crude product was purified by column (50%-100% AcOEt/PE gradient), yielding tert-butyl 3-(2-bromothiazole-5-carboxamido)-5-(4-fluorophenyl)-1H-pyrazole-1-carboxylate (160 mg, 20%) as a white solid.

Workup

  1. washwashed with water
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column (50%-100% AcOEt/PE gradient)

Sources & evidence

ORD record
ord-e974354b4a52401c938e0b41ad0b3a15
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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