Hydrochloric Acid → 3-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid

HRID 1512873노트

반응식

HRID 1512873 반응식
[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]=[CH:21][CH:22]=[C:23]4[C:27]=3[NH:26][CH:25]=[C:24]4[CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[N:15]=2)[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12].Cl>CC(O)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]=[CH:21][CH:22]=[C:23]4[C:27]=3[NH:26][CH:25]=[C:24]4[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[N:15]=2)[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58222445Ethyl 3-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate

생성물 1

HCID 445476033-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid수율 53.3%

시약·촉매·용매 2

HCID 962Water용매HCID 3776Isopropanol용매

반응 조건

온도
70 °C

실험 절차

Sodium hydroxide (15 mg) was added to a solution of ethyl 3-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (D36) (110 mg) in iPrOH (4 mL) and water (4 mL). The resulting mixture was heated at 70° C. for 40 mins. Then 0.5 M HCl solution was added until pH was about 6. The solvent was concentrated, and the residue was dissolved in water. The precipitate was purified by Mass Directed Auto Prep to afford 3-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid (E13) (55 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.40 (6H, d), 2.63 (2H, t), 3.00 (2H, t), 5.46 (1H, m), 7.21 (1H, t), 7.27 (1H, d), 7.82 (1H, d), 7.93 (1H, d), 8.75 (1H, d), 9.06 (1H, d), 10.87 (1H, s), 12.08 (1H, br s). MS (ES): C21H19ClN4O4 requires 426. found 427.1 (M+H+).

후처리

  1. concentrationThe solvent was concentrated
  2. dissolutionthe residue was dissolved in water
  3. customThe precipitate was purified by Mass Directed Auto Prep

출처 및 근거

ORD 기록
ord-f2671b48b8e9411e912190cc744f0770
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217028B2

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