Acetic Acid → HCID 70979776, compound

HRID 882221Notes

Reaction equation

HRID 882221 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][N:15]=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].[OH-].[Li+].C(O)(=O)C>C(O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][N:15]=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

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 86709413HCID 86709413, compound

Product 1

HCID 70979776HCID 70979776, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 6-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)nicotinate (for a preparation see Intermediate 6) (580 mg, 1.273 mmol) in ethanol (10 mL) was treated with a aqueous lithium hydroxide solution (1N, 2.55 mL, 2.55 mmol) and the resulting mixture was stirred for 2 h. The bulk of ethanol was evaporated in vacuo and the residue was diluted with water (ca. 5 mL). The cloudy mixture was treated with acetic acid (0.146 mL, 2.55 mmol) and the precipitate formed was isolated by filtration, washed with Et2O and dried at 60° C. for 16 h to give 6-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)nicotinic acid (410 mg, 0.959 mmol, 75% yield) as a pale yellow solid which was used in the next step without further purification. LCMS (HpH, 2 min), Rt=0.63 min, MH+=428.

Workup

  1. customThe bulk of ethanol was evaporated in vacuo
  2. additionthe residue was diluted with water (ca. 5 mL)
  3. customthe precipitate formed
  4. customwas isolated by filtration
  5. washwashed with Et2O
  6. customdried at 60° C. for 16 h

Sources & evidence

ORD record
ord-7117f9aba1f9444bbf3d9bbfc523bdbd
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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