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Ethanolamine → 2-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)-N-(2-hydroxyethyl)acetamide

HRID 2278786
ノート
印刷プレビュー

反応式

HRID 2278786 の反応式
[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:27]=[C:26]([CH3:28])[C:20]([O:21][CH2:22][C:23]([OH:25])=O)=[C:19]([CH2:29][CH3:30])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:31][CH3:32])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:55]([CH2:57][NH2:58])[OH:56]>C1COCC1.O.C([O-])(O)=O.[Na+]>[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:27]=[C:26]([CH3:28])[C:20]([O:21][CH2:22][C:23]([NH:58][CH2:57][CH2:55][OH:56])=[O:25])=[C:19]([CH2:29][CH3:30])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:31][CH3:32])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 575243792-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)acetic acid

生成物 1

HCID 575245322-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)-N-(2-hydroxyethyl)acetamide
収率 25.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 2-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)acetic acid (780 mg, 1.65 mmol) in THF (30 mL), HOBt (267 mg, 1.98 mmol) followed by EDC HCl (379 mg, 1.98 mmol) is added. The mixture is stirred at rt for 5 min before ethanolamine (121 mg, 1.98 mmol) is added. Stirring is continued for 3 h. The mixture is diluted with water and sat. aq. NaHCO3 solution and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by prep. HPLC to give the title compound (202 mg) as a colourless oil; LC-MS: tR=1.07 min, [M+H]+=481.01; 1H NMR (CDCl3): δ 7.90 (s, 1H), 7.89 (s, 1H), 7.50 (d, J=0.5 Hz, 1H), 7.35 (t br, J=5.3 Hz, 1H), 7.30 (d, J=0.8 Hz, 1H), 4.39 (s, 2H), 4.02 (s, 3H), 3.87 (t, J=4.9 Hz, 2H), 3.63 (m, 2H), 3.51 (s, 2H), 3.20-3.29 (m, 1H), 2.73 (q, J=7.6 Hz, 2H), 2.38 (s, 3H), 2.06-2.15 (m, 2H), 1.84-1.95 (m, 4H), 1.70-1.80 (m, 2H), 1.33 (t, J=7.6 Hz, 3H).

後処理

  1. additionis added
  2. additionis added
  3. extractionextracted twice with EA
  4. dry with materialextracts are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by prep

出典と根拠

ORDレコード
ord-4e06637e28be4ea5a0e3938fa8b6412f
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133179B2

反応ノート

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