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methyl 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate → 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acid

HRID 1399791
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HRID 1399791 반응식
[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:12][C:13]([C:14]([O:16]C)=[O:15])=[C:8]2[N:7]=[C:6]1[CH3:24]>[Li+].[OH-].C1COCC1>[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[C:8]2[N:7]=[C:6]1[CH3:24]
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참가 물질

4

반응물 1

HCID 89648260methyl 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

생성물 1

HCID 716106943-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acid수율 63%

시약·촉매·용매 2

HCID 3939Lithium Hydroxide용매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

A mixture of methyl 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate (239 mg, 0.55 mmol) in 2N LiOH (15 mL) and THF (15 mL) was stirred at 60° C. for 5 h. It was cooled to room temperature and the precipitate was collected by filtration. It was then poured into water (50 mL) and the suspension was acidified with formic acid to pH=1. It was filtered and the solid was washed with water to afford the desired product as a gray solid (146 mg, 63%); LC/MS: MS (ES+) m/e 421 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.46 (s, 3H), 3.39 (t, J=4.8 Hz, 4H), 3.67 (t, J=4.8 Hz, 4H), 5.50 (s, 2H), 6.67 (d, J=4.5 Hz, 1H), 7.04 (s, 1H), 7.28 (t, J=7.5 Hz, 1H), 7.60 (d, J=4.5 Hz, 1H), 8.14 (s, 1H).

후처리

  1. temperatureIt was cooled to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. additionIt was then poured into water (50 mL)
  4. filtrationIt was filtered
  5. washthe solid was washed with water

출처 및 근거

ORD 기록
ord-4461bd9a640f485b870c29e1cba5f220
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08906910B2

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