Sodium Carbonate → 5-Amino-1-(1-methyl-2-oxo-2-phenyl-ethyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 63776

Reaction equation

HRID 63776 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][C:10]=1[NH2:11])=[O:5])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].Br[CH:19]([CH3:28])[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21].CCOC(C)=O.CCCCCC>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH:19]([CH3:28])[C:20](=[O:21])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]=1[NH2:11])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 164522-BromopropiophenoneHCID 81472ethyl 3-amino-1H-pyrazole-4-carboxylateHCID 21226206Ethyl acetate hexane

Product 1

HCID 576322195-Amino-1-(1-methyl-2-oxo-2-phenyl-ethyl)-1H-pyrazole-4-carboxylic acid ethyl esterYield 12%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Amino-1H-pyrazole-4-carboxylic acid ethyl ester (7.35 g, 47.3 mmol) was dissolved in 160 mL of DMF. Na2CO3 (5.02 g, 47.3 mmol) was added followed by 2-bromopropiophenone (7.2 mL, 47.3 mmol). The reaction stirred at room temperature for 2 days. The solution was diluted with AcOEt and the organic layer was washed with sat. NaHCO2, brine, dried (MgSO4), and concentrated. Flash chromatography (20-45% AcOEt/hexane) gave the desired product (1.58 g, 12% yield). 1H NMR (400 MHz, CDCl3) δ 1.3 (t, J=7.0 Hz, 3H), 1.7 (d, J=7.4 Hz, 3H), 4.2 (q, J=7.0 Hz, 2H), 5.4 (bs, 2H), 5.9 (q, J=7.0 Hz, 1H), 7.41-7.59 (m, 3H), 7.60 (s, 1H), 8.0 (d, J=8.0 Hz, 2H).

Workup

  1. washthe organic layer was washed with sat. NaHCO2, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bcd5d5e389944efd89d9a142e61aebcd
Source dataset
uspto-grants-2016_09
Patent number
US09447100B2

Linked notes

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