Acetic Acid → HCID 70976697, compound

HRID 882237Notes

Reaction equation

HRID 882237 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][N:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:6][C@@H:5]1[CH3:32])(=[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:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][N:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 70976481HCID 70976481, compound

Product 1

HCID 70976697HCID 70976697, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 6-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)nicotinate (for a preparation see Intermediate 27)(240 mg, 0.557 mmol) in ethanol (5 mL) was treated with aqueous lithium hydroxide (1N, 1.115 mL, 1.115 mmol) and the resulting mixture was stirred at room temperature. After 1 h most of the ethanol was removed in vacuo, the residue was diluted with water (ca 2 mL) and the “cloudy” mixture was treated with acetic acid (0.064 mL, 1.115 mmol). 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-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)nicotin ic acid (150 mg, 0.373 mmol, 66.9% yield) as a pale yellow solid which was used in the next step without further purification. LCMS (HpH, 2 min), Rt=0.61 min, MH+=403.

Workup

  1. customAfter 1 h most of the ethanol was removed in vacuo
  2. additionthe residue was diluted with water (ca 2 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-ae85e1e85118480b96c32959f66c308a
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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