Sodium Hydroxide → HCID 70976494, compound

HRID 882234Notes

Reaction equation

HRID 882234 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][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2].[OH-].[Na+]>CO>[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][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 70976599HCID 70976599, compound

Product 1

HCID 70976494HCID 70976494, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 22)(700 mg, 1.685 mmol) was dissolved in MeOH (10 ml) and sodium hydroxide solution (2M, 1.68 ml, 3.37 mmol) was added. After 6.5 h a further 2 equivalents of sodium hydroxide (2M, 1.685 ml) was added and reaction mixture stirred overnight. The was concentrated and the residue was diluted with water. Hydrochloric acid (2N, 1 ml) was added forming a precipitate which was isolated by filtration and dried to give 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (500 mg, 1.245 mmol, 73.9% yield) as a pinky solid. The aqueous phase was extracted EtOAc (×3) and the combined organic phases were dried over MgSO4 then concentrated in vacuo to give a further batch of 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (140 mg, 0.349 mmol, 20.70% yield) as a yellow foam. LCMS (HpH, 2 min), Rt=0.62 min, MH+=402.

Workup

  1. customreaction mixture
  2. concentrationThe was concentrated
  3. additionthe residue was diluted with water
  4. additionHydrochloric acid (2N, 1 ml) was added
  5. customforming a precipitate which
  6. customwas isolated by filtration
  7. customdried

Sources & evidence

ORD record
ord-4d8fc8391c454c19857ac2415b8960c9
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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