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Hydroxyamine hydrochloride → (S)-1-[3-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-3-{1-[2-(4-fluorophenyl)-2-hydroxyimino-ethyl]-piperidin-3-ylmethyl}-urea

HRID 896562
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HRID 896562 반응식
[CH2:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH:18][CH2:19][C@@H:20]2[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][C:27]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=O)[CH2:21]2)=[O:17])[CH:6]=[C:7]([C:9]2[N:13]([CH3:14])[N:12]=[N:11][N:10]=2)[CH:8]=1)[CH3:2].Cl.[NH2:37][OH:38]>N1C=CC=CC=1>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH:18][CH2:19][C@@H:20]2[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][C:27]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[N:37][OH:38])[CH2:21]2)=[O:17])[CH:6]=[C:7]([C:9]2[N:13]([CH3:14])[N:12]=[N:11][N:10]=2)[CH:8]=1)[CH3:2]
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참가 물질

4

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 69736343(S)-1-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-3-{1-[2-(4-fluorophenyl)-2-oxo-ethyl]-piperidin-3-ylmethyl}-urea

생성물 1

HCID 86591726(S)-1-[3-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-3-{1-[2-(4-fluorophenyl)-2-hydroxyimino-ethyl]-piperidin-3-ylmethyl}-urea수율 50%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of (S)-1-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-3-{l-[2-(4-fluorophenyl)-2-oxo-ethyl]-piperidin-3-ylmethyl}-urea (20 mg, 42 μmol) in pyridine (0.5 mL) was treated with hydroxylamine hydrochloride (6 mg, 82 μmol) and stirred at room temperature for 16 hours. The solution was concentrated under vacuum, and the residue was purified by flash chromatography, eluting with 2.5% methanol in dichloromethane, containing 0.25% aqueous ammonia, to provide a white glassy solid (10 mg, 50%). 1H NMR (300 MHz, CDCl3) δ8.14 (s, 1H), 7.59 (s, 1H), 7.54 (m, 2H), 7.48 (s, 1H), 7.28 (s, 1H), 7.00 (t, J=9 Hz, 2H), 6.15 (bt, 1H), 4.16 (s, 3H), 3.78 (ab, J=15 Hz, 2H), 3.19 (m, 2H), 3.06 (m, 1H), 2.95 (m, 1H), 2.60 (q, J=8 Hz, 2H), 2.26 (m, 1H), 2.09 (m, 1H), 1.78 (m, 3H), 1.60 (m, 1H), 1.19 (t, J=8 Hz, 3H), 1.10 (m, 1H). Mass spec (ES+) m/z 495.4 (M+H+).

후처리

  1. concentrationThe solution was concentrated under vacuum
  2. customthe residue was purified by flash chromatography
  3. washeluting with 2.5% methanol in dichloromethane
  4. additioncontaining 0.25% aqueous ammonia

출처 및 근거

ORD 기록
ord-7ec81ed202824c56b0925935cef17b28
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06919356B2

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