ethyl 1-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)-3-t-butyl-1H-pyrazole-5-carboxylate → ethyl 3-t-butyl-1-(2-oxo-1,2-dihydroquinolin-6-yl)-1H-pyrazole-5-carboxylate

HRID 1696543Notes

Reaction equation

HRID 1696543 reaction equation
COC1C=CC(C[N:8]2[C:17]3[C:12](=[CH:13][C:14]([N:18]4[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][C:20]([C:28]([CH3:31])([CH3:30])[CH3:29])=[N:19]4)=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:32])=CC=1>C(O)(C(F)(F)F)=O>[C:28]([C:20]1[CH:21]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:18]([C:14]2[CH:13]=[C:12]3[C:17](=[CH:16][CH:15]=2)[NH:8][C:9](=[O:32])[CH:10]=[CH:11]3)[N:19]=1)([CH3:29])([CH3:30])[CH3:31]

Participants

3

Reactant 1

HCID 67271613ethyl 1-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)-3-t-butyl-1H-pyrazole-5-carboxylate

Product 1

HCID 67272483ethyl 3-t-butyl-1-(2-oxo-1,2-dihydroquinolin-6-yl)-1H-pyrazole-5-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ethyl 1-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)-3-t-butyl-1 H-pyrazole-5-carboxylate (1.5 g, 3.3 mmol) in TFA (25 mL) was heated in a sealed tube at 100° C. for 7 h. The mixture was cooled, concentrated and purified by silica gel column chromatography to yield ethyl 3-t-butyl-1-(2-oxo-1,2-dihydroquinolin-6-yl)-1H-pyrazole-5-carboxylate (1.0 g, 90% yield). 1H NMR (400 MHz, CDCl3): δ 7.95 (d, J=9.6 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 7.66 (dd, J=2.4, and 8.4 Hz, 1H), 7.46 (d, J=8.8 Hz, 1H), 6.94 (s, 1H), 6.82 (d, J=9.2 Hz, 1H). LC-MS (EI) m/z: 340.3 (M+H+).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-861b02f0dbb7413984327fbb17723c16
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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