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Toluene → 6-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-N-(tetrahydro-pyran-4-yl)-nicotinamide

HRID 1514681
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HRID 1514681 반응식
C[Al](C)C.[NH2:5][CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.C[O:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[C:24]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[N:25][O:26][C:27]=2[CH2:28][OH:29])=[N:17][CH:16]=1.C1(C)C=CC=CC=1>O1CCOCC1>[F:36][C:33]1[CH:34]=[CH:35][C:30]([C:24]2[C:23]([CH2:22][O:21][C:18]3[CH:19]=[CH:20][C:15]([C:14]([NH:5][CH:6]4[CH2:11][CH2:10][O:9][CH2:8][CH2:7]4)=[O:13])=[CH:16][N:17]=3)=[C:27]([CH2:28][OH:29])[O:26][N:25]=2)=[CH:31][CH:32]=1
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참가 물질

6

반응물 4

HCID 1140TolueneHCID 4192234-Aminotetrahydropyran2회HCID 16682925Trimethylaluminum2회HCID 667181316-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

생성물 1

HCID 469285706-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-N-(tetrahydro-pyran-4-yl)-nicotinamide수율 27%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

반응 조건

온도
85 °C

실험 절차

A trimethylaluminium solution (2 M in toluene, 418 μL, 0.84 mmol) was added to a solution of 4-aminotetrahydropyran (87.2 mg, 0.84 mmol) in dioxane (3.75 mL). 6-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (75.0 mg, 0.21 mmol) in dioxane (3.75 mL) was added after 1 h at 50° C. The reaction mixture was stirred at 85° C. overnight. Again trimethylaluminium solution in toluene (2 M in toluene, 418 μL, 0.84 mmol) and 4-aminotetrahydropyran (87.2 mg, 0.84 mmol) were added and stirring was continued for 3 h at 85° C. The solvent was removed by distillation. The residue was purified by chromatography (Isolute® SPE flash NH2 column, ethyl acetate:heptane=1:1 to 9:1) to afford the title compound (24 mg, 27%) as white solid. MS: m/e=428.2 [M+H]+.

후처리

  1. stirringstirring
  2. waitwas continued for 3 h at 85° C
  3. customThe solvent was removed by distillation
  4. customThe residue was purified by chromatography (Isolute® SPE flash NH2 column, ethyl acetate:heptane=1:1 to 9:1)

출처 및 근거

ORD 기록
ord-81d9cc645a694747aa5706443a42546d
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08222246B2

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