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Sodium Hydroxide → 6-(2-(Tert-butoxycarbonyl(isopropyl)-amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylic acid

HRID 1958483
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HRID 1958483 반응식
[C:1]([O:5][C:6]([N:8]([CH:34]([CH3:36])[CH3:35])[C:9]1[S:10][C:11]([C:14]2[CH:15]=[C:16]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:17]3[N:18]([CH:20]=[C:21]([C:23]([O:25]CC)=[O:24])[N:22]=3)[CH:19]=2)=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]([CH:34]([CH3:36])[CH3:35])[C:9]1[S:10][C:11]([C:14]2[CH:15]=[C:16]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:17]3[N:18]([CH:20]=[C:21]([C:23]([OH:25])=[O:24])[N:22]=3)[CH:19]=2)=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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반응물 2

HCID 14798Sodium HydroxideHCID 58208025Ethyl 6-(2-(tert-butoxycarbonyl-(isopropyl)amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate

생성물 1

HCID 582079096-(2-(Tert-butoxycarbonyl(isopropyl)-amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylic acid수율 98.2%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

A solution of ethyl 6-(2-(tert-butoxycarbonyl-(isopropyl)amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate (1.00 g, 2.0 mmol) in THF/MeOH (2:1, 15 mL) was treated with 1 N NaOH (5 mL, 5 mmol) at room temperature for 5 hours. The organic solvents were removed under vacuum and the aqueous residue was acidified with 1 N HCl and the solids extracted into CH2Cl2. The extracts were washed with water and concentrated to give 940 mg of 6-(2-(tert-butoxycarbonyl(isopropyl)-amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylic acid as a yellow solid. LCMS (Conditions C): 3.98 min (RT); (M+H)+=479.43 (100%).

후처리

  1. customThe organic solvents were removed under vacuum
  2. extractionthe solids extracted into CH2Cl2
  3. washThe extracts were washed with water
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8ef1b72511144bcf83d79d8ca0b38bf3
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410128B2

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