Hydrochloric Acid → (2E)-N-[4-(aminomethyl)phenyl]-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylamide

HRID 30719Notes

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:33]=[CH:32][C:22]([CH2:23][NH:24]C(=O)OC(C)(C)C)=[CH:21][CH:20]=2)=[O:17])=[CH:4][CH:3]=1.Cl>C(OCC)(=O)C>[NH2:24][CH2:23][C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:16](=[O:17])/[CH:15]=[CH:14]/[C:9]2[CH:10]=[N:11][N:12]([CH3:13])[C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of tert-butyl [4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)benzyl]carbamate (2.0 g) and 4N hydrogenchloride in ethyl acetate (80 mL) was stirred at 70° C. for 15 hrs. The precipitated crystals were collected by filtration and washed with ethyl acetate. A 1N aqueous sodium hydroxide solution (50 mL) was added to the obtained crystals (0.30 g) and the mixture was extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give (2E)-N-[4-(aminomethyl)phenyl]-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylamide as colorless crystals (0.18 g). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 201-202° C.

Workup

filtrationThe precipitated crystals were collected by filtration
washwashed with ethyl acetate
additionA 1N aqueous sodium hydroxide solution (50 mL) was added to the obtained crystals (0.30 g)
extractionthe mixture was extracted with ethyl acetate-tetrahydrofuran
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-67a5f3feba6549bfa7879be7acd7c4f3
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423159B2

Reaction notes

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