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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
ノート
印刷プレビュー

反応式

HRID 896562 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 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}-urea収率 50%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-7ec81ed202824c56b0925935cef17b28
出典データセット
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06919356B2

反応ノート

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