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 882253ノート

反応式

HRID 882253 の反応式
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]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 86709421HCID 86709421、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6275e6fd1dda4c2cb08d3977dabfc2f1
出典データセット
uspto-grants-2015_03
特許番号
US08993554B2

反応ノート

読み込み中…