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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
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HRID 2278786 반응식
[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
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참가 물질

8

반응물 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

생성물 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
수율 25.5%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4e06637e28be4ea5a0e3938fa8b6412f
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133179B2

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