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

HRID 1512944
ノート
印刷プレビュー

反応式

HRID 1512944 の反応式
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[CH:22]4)[N:15]=2)[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12].Cl>C1COCC1.C(O)(C)C.O>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:22]4)[N:15]=2)[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:12])[CH3:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58222470Ethyl 3-[5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]propanoate

生成物 1

HCID 445471733-[5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]propanoic acid収率 37.5%

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 3776Isopropanol溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydroxide (24 mg) was added to a solution of ethyl 3-[5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]propanoate (D115) (54 mg) in THF (1 mL), isopropanol (1 mL) and water (0.5 mL). The reaction mixture was stirred at room temperature until LCMS showed no starting material. 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-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]propanoic acid (E90) (19 mg). δH (DMSO-d6, 400 MHz): 1.39 (6H, d), 2.70 (2H, t), 2.99 (2H, t), 5.46 (1H, m), 6.34 (1H, s), 7.45 (1H, d), 7.76 (1H, dd), 8.22 (1H, s), 8.55 (1H, d), 8.93 (1H, d), 11.35 (1H, s), 12.26 (1H, s); MS (ES): C21H19ClN4O4 requires 426; found 427.1 (M+H+).

後処理

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

出典と根拠

ORDレコード
ord-3f6911687f544fcc942c24f5c5f9b871
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08217028B2

反応ノート

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