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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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1-Hydroxybenzotriazole → 7-Methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-2-{5-[2-(1-oxidothiomorpholin-4-yl)-2-oxoethyl]-4,5-dihydro-1,3-thiazol-2-yl}-1H-indole

HRID 1042206
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HRID 1042206 반응식
Cl.[NH:2]1[CH2:7][CH2:6][S:5](=[O:8])[CH2:4][CH2:3]1.[CH3:9][C:10]1[CH:11]=[C:12]([O:28][C:29]2[CH:30]=[N:31][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][CH:34]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]([CH2:24][C:25](O)=[O:26])[CH2:22][N:23]=1)=[CH:15]2.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(N(CC)CC)C>[CH3:9][C:10]1[CH:11]=[C:12]([O:28][C:29]2[CH:30]=[N:31][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][CH:34]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]([CH2:24][C:25]([N:2]3[CH2:7][CH2:6][S:5](=[O:8])[CH2:4][CH2:3]3)=[O:26])[CH2:22][N:23]=1)=[CH:15]2
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참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 204414791Lambda4-thiomorpholin-1-one hydrochlorideHCID 58081062[2-(7-Methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid

생성물 1

HCID 58081038
7-Methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-2-{5-[2-(1-oxidothiomorpholin-4-yl)-2-oxoethyl]-4,5-dihydro-1,3-thiazol-2-yl}-1H-indole
수율 42.4%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a solution of thiomorpholine 1-oxide hydrochloride (140 mg) and triethylamine (0.125 mL) in N,N-dimethylformamide (15 mL) were added [2-(7-methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid (200 mg), 1-hydroxybenzotriazole (121 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (172 mg) under ice-cooling, and the mixture was stirred under ice-cooling and then at room temperature for 15 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:methanol=100:0 to 75:25, volume ratio), and the obtained pale-yellow crystals were recrystallized from ethyl acetate-hexane to give the title compound (104 mg, yield 42%) as colorless crystals.

후처리

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained pale-yellow crystals were recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-091d881f06124435b42c8fe22d76f940
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08557805B2

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