2-Ethyl-5-phenyl-2H-pyrazole-3-carboxylic Acid Methoxy-methyl-amide → [4-(2-Ethyl-5-phenyl-2H-pyrazol-3-yl)-4-oxo-but-2-ynyl]-carbamic Acid Tert-Butyl Ester

HRID 396406Notes

Reaction equation

HRID 396406 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]#[CH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.CON(C)[C:20]([C:22]1[N:23]([CH2:33][CH3:34])[N:24]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:26]=1)=[O:21]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]#[C:11][C:20]([C:22]1[N:23]([CH2:33][CH3:34])[N:24]=[C:25]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:26]=1)=[O:21])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 98783462-Ethyl-5-phenyl-2H-pyrazole-3-carboxylic Acid Methoxy-methyl-amideHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 178418339Butyllithium

Product 1

HCID 10291654[4-(2-Ethyl-5-phenyl-2H-pyrazol-3-yl)-4-oxo-but-2-ynyl]-carbamic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a −10° C. solution of N-t-butoxycarbonyl propargylamine (502 mg, 3.24 mmoles) in THF (5 mL) was added nBuLi (3.7 mL of a 1.6 M solution in hexanes, 5.94 mmoles) dropwise over 10 minutes. The resulting dianion mixture was stirred at −10° C. for 15 minutes, then treated with a THF solution (2 mL) of the above-prepared 2-ethyl-5-phenyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide (125 mg, 482 μmoles), allowed to warm to room temperature, and stirred at room temperature for 2 hours. The resulting mixture was cooled to 0° C., quenched with 2 M NaH2PO4, diluted with ethyl acetate, and vigorously stirred for 5 minutes. The phases were separated, the organic phase dried over Na2SO4, filtered, and concentrated in vacuo. The crude title compound was used directly in the next step.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature for 2 hours
  3. temperatureThe resulting mixture was cooled to 0° C.
  4. customquenched with 2 M NaH2PO4
  5. additiondiluted with ethyl acetate
  6. stirringvigorously stirred for 5 minutes
  7. customThe phases were separated
  8. dry with materialthe organic phase dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48384bed6520495b84390a86f78a3863
Source dataset
uspto-grants-2003_08
Patent number
US06608087B1

Reaction notes

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