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Hydrochloric Acid → 3-(5-{5-[6-[(1-methylethyl)oxy]-5-(methyloxy)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-2-yl)propanoic acid

HRID 1512947
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인쇄 미리보기

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HRID 1512947 반응식
[OH-].[Na+].[CH3:3][CH:4]([O:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[CH:21]4)[N:14]=2)=[CH:9][C:8]=1[O:34][CH3:35])[CH3:5].Cl>C1COCC1.C(O)(C)C.O>[CH3:5][CH:4]([O:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:21]4)[N:14]=2)=[CH:9][C:8]=1[O:34][CH3:35])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59146075Ethyl 3-(5-{5-[6-[(1-methylethyl)oxy]-5-(methyloxy)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-2-yl)propanoate

생성물 1

HCID 591461693-(5-{5-[6-[(1-methylethyl)oxy]-5-(methyloxy)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-2-yl)propanoic acid수율 15.2%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 3776Isopropanol용매
HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydroxide (3 mg) was added to a solution of ethyl 3-(5-{5-[6-[(1-methylethyl)oxy]-5-(methyloxy)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-2-yl)propanoate (D118) (35 mg) in THF (5 mL), isopropanol (5 mL) and water (2.5 mL). The reaction mixture was stirred at room temperature overnight. The mixture was neutralized with 2 M HCl till pH ˜6.0. The crude product was purified by Mass Directed Auto Prep to afford 3-(5-{5-[6-[(1-methylethyl)oxy]-5-(methyloxy)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-2-yl)propanoic acid (E93) (5 mg). δH (DMSO-d6, 400 MHz): 1.35 (6H, d), 2.70 (2H, t), 2.99 (2H, t), 3.94 (3H, s), 5.42 (1H, m), 6.34 (1H, s), 7.45 (1H, d), 7.76 (1H, dd), 7.83 (1H, d), 8.23 (1H, s), 8.54 (1H, d), 11.34 (1H, s), 12.26 (1H, s); MS (ES): C22H22N4O5 requires 422; found 423.2 (M+H+).

후처리

  1. customThe crude product was purified by Mass Directed Auto Prep

출처 및 근거

ORD 기록
ord-0952c3aec29b41f797c1b71ae351270a
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08217028B2

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