Acetic Acid → 5-((2S,4R)-1-acetyl-4-((5-cyanopyrazin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinic acid

HRID 882253노트

반응식

HRID 882253 반응식
O.[OH-].[Li+].[C:4]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([O:25]C)=[O:24])=[N:21][CH:22]=3)=[CH:14][CH:15]=2)[C@H:10]([NH:27][C:28]2[CH:33]=[N:32][C:31]([C:34]#[N:35])=[CH:30][N:29]=2)[CH2:9][C@@H:8]1[CH3:36])(=[O:6])[CH3:5].C(O)(=O)C>O.O1CCOCC1>[C:4]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([OH:25])=[O:24])=[N:21][CH:22]=3)=[CH:14][CH:15]=2)[C@H:10]([NH:27][C:28]2[CH:33]=[N:32][C:31]([C:34]#[N:35])=[CH:30][N:29]=2)[CH2:9][C@@H:8]1[CH3:36])(=[O:6])[CH3:5]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 86709421HCID 86709421, 화합물

생성물 1

HCID 867094225-((2S,4R)-1-acetyl-4-((5-cyanopyrazin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinic acid수율 43%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

Lithium hydroxide monohydrate (83 mg, 1.97 mmol) in water (5 mL) was added to methyl 5-((2S,4R)-1-acetyl-4-((5-cyanopyrazin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinate (for a preparation, see Intermediate 52) (435 mg, 0.983 mmol) in 1,4-dioxane (5 mL) and the reaction mixture stirred at room temperature for 70 mins. Acetic acid (0.169 mL, 2.95 mmol) was added and the resulting mixture stirred for 10 mins. The mixture was filtered, the solid collected was washed with water, then dried in a vacuum oven to give 5-((2S,4R)-1-acetyl-4-((5-cyanopyrazin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinic acid (181 mg, 0.422 mmol, 43% yield) as a brown solid. LCMS: (Formate, 2 min) Rt=0.66 mins, MH+=429.

후처리

  1. customfor a preparation
  2. stirringthe resulting mixture stirred for 10 mins
  3. filtrationThe mixture was filtered
  4. customthe solid collected
  5. washwas washed with water
  6. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-6275e6fd1dda4c2cb08d3977dabfc2f1
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993554B2

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