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Acetic Acid → 5-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2H-pyrazole-3-carboxylic acid methyl ester

HRID 1695495
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HRID 1695495 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH:13]=O)=[C:11]([CH3:15])[O:10][N:9]=2)=[CH:4][CH:3]=1.Cl.[CH3:17][O:18][C:19]([C:21]1[NH:22][N:23]=[C:24]([NH2:26])[CH:25]=1)=[O:20].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:17][O:18][C:19]([C:21]1[NH:22][N:23]=[C:24]([NH:26][CH2:13][C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][O:10][C:11]=2[CH3:15])[CH:25]=1)=[O:20]
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참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 167282913-(4-Fluorophenyl)-5-methylisoxazole-4-carboxaldehydeHCID 50998527Methyl 3-Amino-1H-pyrazole-5-carboxylate hydrochloride

생성물 1

HCID 666437475-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2H-pyrazole-3-carboxylic acid methyl ester수율 44%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 3-(4-fluoro-phenyl)-5-methyl-isoxazole-4-carbaldehyde (1.75 g, 8.53 mmol) and the 5-amino-2H-pyrazole-3-carboxylic acid methyl ester hydrochloride (1.2 g, 8.53 mmol) in methanol (70 mL) at room temperature was added molecular sieves (2.5 g) and then after 1 h, acetic acid (6.8 mL, 119.4 mmol) was added. Then sodium cyanoborohydride (1.07 g, 17.1 mmol) was added portionwise and the mixture stirred at room temperature overnight. After evaporation, dichloromethane was added and the mixture washed with sodium hydrogen carbonate (saturated solution). The organic layer was then dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica, heptane:ethyl acetate 7:3 to 6:4) afforded 5-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2H-pyrazole-3-carboxylic acid methyl ester (1.2 g, 44%).

후처리

  1. customAfter evaporation, dichloromethane
  2. additionwas added
  3. washthe mixture washed with sodium hydrogen carbonate (saturated solution)
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, heptane:ethyl acetate 7:3 to 6:4)

출처 및 근거

ORD 기록
ord-6594fc062f1b4b8c8c7a10c930299972
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163728B2

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