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

HRID 30719
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인쇄 미리보기

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HRID 30719 반응식
[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
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참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 86602528tert-butyl [4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)benzyl]carbamate

생성물 1

HCID 69206814(2E)-N-[4-(aminomethyl)phenyl]-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylamide수율 11.6%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-67a5f3feba6549bfa7879be7acd7c4f3
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07423159B2

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