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1-Hydroxybenzotriazole → HCID 66726121, 화합물

HRID 1042197
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HRID 1042197 반응식
O1CCCC1.[CH2:6]([NH2:8])[CH3:7].[CH2:9]([C:11]1[CH:12]=[C:13]([O:29][C:30]2[CH:31]=[N:32][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:34][CH:35]=2)[CH:14]=[C:15]2[C:19]=1[NH:18][C:17]([C:20]1[S:21][CH:22]([CH2:25][C:26](O)=[O:27])[CH2:23][N:24]=1)=[CH:16]2)[CH3:10].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[CH2:6]([NH:8][C:26](=[O:27])[CH2:25][CH:22]1[S:21][C:20]([C:17]2[NH:18][C:19]3[C:15]([CH:16]=2)=[CH:14][C:13]([O:29][C:30]2[CH:31]=[N:32][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:34][CH:35]=2)=[CH:12][C:11]=3[CH2:9][CH3:10])=[N:24][CH2:23]1)[CH3:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58081018HCID 58081018, 화합물HCID 66726184Ethylamine tetrahydrofuran

생성물 1

HCID 66726121HCID 66726121, 화합물수율 44%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

실험 절차

To a mixed solution of 2.0M-ethylamine tetrahydrofuran solution (0.33 mL), [2-(7-ethyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid (200 mg), and N,N-dimethylformamide (10 mL) were added 1-hydroxybenzotriazole (89 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (125 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 90:10, volume ratio), and the obtained pale-yellow oil was recrystallized from ethyl acetate-hexane to give the title compound (92 mg, yield 44%) 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 oil was recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-798895ee59514accab854e668e6f5d88
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08557805B2

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