HCID 86665172, compound → HCID 66871916, compound

HRID 1893720Notes

Reaction equation

HRID 1893720 reaction equation
[CH3:1][Mg]Br.[CH3:4][O:5][C:6]1[CH:36]=[CH:35][C:9]([CH2:10][N:11]2[CH:15]=[C:14]([C:16]3[N:17]=[C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=4)[S:19][CH:20]=3)[C:13]([C:29](N(OC)C)=[O:30])=[N:12]2)=[CH:8][CH:7]=1>C1COCC1.CCOC(C)=O.Cl>[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[CH:15]=[C:14]([C:16]3[N:17]=[C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=4)[S:19][CH:20]=3)[C:13]([C:29](=[O:30])[CH3:1])=[N:12]2)=[CH:35][CH:36]=1

Participants

6

Reactant 2

HCID 86665172HCID 86665172, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 66871916HCID 66871916, compoundYield 101%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

According to Scheme 5, Step 5: Methylmagnesium bromide 3 M (148 μmol, 49 μL) was added dropwise at room temperature to a solution of 1-(4-methoxybenzyl)-N-methoxy-N-methyl-4-(2-(6-methylpyridin-2-yloxy)thiazol-4-yl)-1H-pyrazole-3-carboxamide (99 μmol, 46 mg) in THF (0.5 mL) and the reaction mixture was stirred for 1 hour at room temperature. The reaction was diluted with EtOAc and with an aqueous solution of HCl 1M. The aqueous phase was extracted with EtOAc. The organic phase was dried over Na2SO4, was filtered and was concentrated to yield 1-(1-(4-methoxybenzyl)-4-(2-(6-methylpyridin-2-yloxy)thiazol-4-yl)-1H-pyrazol-3-yl)ethanone (0.10 mmol, 42 mg, 100%) as a beige solid. The mixture was used without further purification.

Workup

  1. extractionThe aqueous phase was extracted with EtOAc
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationwas filtered
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-68b44f6f323b4078a7b8caf45b21df99
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

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