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

HRID 882242Notes

Reaction equation

HRID 882242 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([O:22]C)=[O:21])=[N:18][CH:19]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][N:26]=2)[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2].O.[OH-].[Li+].C(O)(=O)C>O1CCOCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([OH:22])=[O:21])=[N:18][CH:19]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][N:26]=2)[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 70976546HCID 70976546, compound

Product 1

HCID 867094165-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinic acidYield 68.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinate (for a preparation see Intermediate 33)(2.94 g, 6.66 mmol) was dissolved in anhydrous 1,4-dioxane (20 ml). Water (20.0 ml) was added followed by lithium hydroxide (0.319 g, 13.32 mmol) and reaction mixture stirred at r.t. After 1 h, the 1,4-dioxane was removed in vacuo and aqueous residue was treated with acetic acid (1.144 ml, 19.98 mmol). The resulting orange precipitate was stirred for 20 min, isolated by filtration, washed with water and dried under vacuum overnight to give 5-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinic acid (2.16 g, 4.55 mmol, 68.3% yield) as a brown solid. LCMS (Formate, 2 min), Rt=0.68 min, MH+=428.

Workup

  1. customthe 1,4-dioxane was removed in vacuo and aqueous residue
  2. stirringThe resulting orange precipitate was stirred for 20 min
  3. customisolated by filtration
  4. washwashed with water
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-fb09dd2e0fce414283b906a6015e02fd
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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