Citric Acid → 5-(3-Aminoisoquinolin-7-yl)-6-methylnicotinic acid

HRID 468920노트

반응식

HRID 468920 반응식
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]1[C:13]([CH3:22])=[N:14][CH:15]=[C:16]([CH:21]=1)[C:17]([O:19]C)=[O:18])[CH:6]=2.O1CCCC1.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]1[C:13]([CH3:22])=[N:14][CH:15]=[C:16]([CH:21]=1)[C:17]([OH:19])=[O:18])[CH:6]=2

참가 물질

5

반응물 4

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67975074Methyl 5-(3-aminoisoquinolin-7-yl)-6-methylnicotinate

생성물 1

HCID 679750675-(3-Aminoisoquinolin-7-yl)-6-methylnicotinic acid수율 63.7%

실험 절차

To a mixture of methyl 5-(3-aminoisoquinolin-7-yl)-6-methylnicotinate (189 mg; 0.6444 mmol) and tetrahydrofuran (4.0 mL; 49 mmol) was added lithium hydroxide (2.0 mL; 2.0 mmol). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was acidified with 10% aqueous citric acid (2 mL), and the resulting yellow precipitate recovered via filtration, washed with water and tetrahydrofuran, and dried under vacuum to yield 114.6 mg of the title compound, which was carried forward without purification. LCMS (ESI): M+H=280.1.

후처리

  1. filtrationthe resulting yellow precipitate recovered via filtration
  2. washwashed with water and tetrahydrofuran
  3. customdried under vacuum

출처 및 근거

ORD 기록
ord-95f853849fb94663a50de9ac8e03ad90
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623889B2

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