Sodium Chloride → 5-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 1695395노트

반응식

HRID 1695395 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([C:21]([OH:23])=O)[N:18]([CH3:20])[N:19]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.[NH2:45][C:46]([CH3:50])([CH3:49])[CH2:47][OH:48].[Cl-].[Na+]>C1COCC1>[OH:48][CH2:47][C:46]([NH:45][C:21]([C:17]1[N:18]([CH3:20])[N:19]=[C:15]([O:14][CH2:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][O:10][C:11]=2[CH3:24])[CH:16]=1)=[O:23])([CH3:50])[CH3:49]

참가 물질

7

반응물 5

HCID 5234Sodium ChlorideHCID 118072-Amino-2-methyl-1-propanolHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 66643617HCID 66643617, 화합물

생성물 1

HCID 595684165-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide수율 95.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (100 mg, 0.3 mmol) in THF (2.7 mL) was added 1-hydroxybenzotriazole hydrate (47.2 mg, 0.3 mmol), N-ethyldiisopropylamine (131.9 μL, 0.76 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimidazole hydrochloride (59.1 mg, 0.3 mmol) and 2-amino-2-methyl-1-propanol (27.8 mg, 0.3 mmol) and the resulting mixture stirred overnight at room temperature. The reaction mixture was then poured into aqueous sodium chloride (saturated) and the mixture was extracted with ethyl acetate. The combined organic layers were then washed with water and saturated sodium hydrogen carbonate solution and then dried over sodium sulfate, filtered and evaporated. Concentration and purification by chromatography (silica, dichloromethane:methanol=99:1 to 95:5) afforded the title compound (115 mg, 94%) as a white solid. MS: m/e=403.2 [M+H]+.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were then washed with water and saturated sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. concentrationConcentration and purification by chromatography (silica, dichloromethane:methanol=99:1 to 95:5)

출처 및 근거

ORD 기록
ord-6edd58e4f6564188a721a0b5ef797ef5
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163728B2

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