Methanesulfonic Acid → (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-{4-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]phenyl}acrylamide

HRID 30718

Reaction equation

HRID 30718 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C:26]([NH:28][NH2:29])=[O:27])=[CH:21][CH:20]=2)=[O:17])=[CH:4][CH:3]=1.[C:30](OCC)(OCC)(OCC)[CH3:31].CS(O)(=O)=O.O1CCCC1>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C:26]3[O:27][C:30]([CH3:31])=[N:29][N:28]=3)=[CH:23][CH:24]=2)=[O:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 8028TetrahydrofuranHCID 66221Triethyl orthoacetateHCID 69209331(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-[4-(2-hydrazino-2-oxoethyl)phenyl]acrylamide

Product 1

HCID 69210253(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-{4-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]phenyl}acrylamideYield 47.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-[4-(2-hydrazino-2-oxoethyl)phenyl]acrylamide (0.50 g), triethyl orthoacetate (0.63 g), methanesulfonic acid (0.025 g), and tetrahydrofuran (10 mL) was heated under reflux for 1 hr. The reaction mixture was diluted with ethyl acetate, washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-{4-[(5-methyl-1,3,4-oxadiazol-2-yl) methyl]phenyl}acrylamide as pale-yellow crystals (0.25 g, yield 46%) from a fraction eluted with ethyl acetate-methanol (100:0-20:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 151-152° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. washwashed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-76a52bfb8fda4b18b22905c1ff77b86f
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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