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 882253Notes

Reaction equation

HRID 882253 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6275e6fd1dda4c2cb08d3977dabfc2f1
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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