Hydrochloric Acid → ((2,3-dihydro(1,4)dioxino(2,3-c) pyridin-7-ylmethyl)(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)acetic acid

HRID 1510767Notes

Reaction equation

HRID 1510767 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][N:6]([CH2:28][C:29]1[N:34]=[CH:33][C:32]2[O:35][CH2:36][CH2:37][O:38][C:31]=2[CH:30]=1)[CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][N:15]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=3)[CH:18]=[CH:17][C:16]2=[O:27])[CH2:9][CH2:8]1)C.[OH-].[Na+].Cl>CO.O1CCCC1>[O:38]1[C:31]2[CH:30]=[C:29]([CH2:28][N:6]([CH2:5][C:4]([OH:39])=[O:3])[CH:7]3[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][N:15]4[C:24]5[C:19](=[N:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=5)[CH:18]=[CH:17][C:16]4=[O:27])[CH2:9][CH2:8]3)[N:34]=[CH:33][C:32]=2[O:35][CH2:36][CH2:37]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57815482ethyl((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)acetate

Product 1

HCID 68928989((2,3-dihydro(1,4)dioxino(2,3-c) pyridin-7-ylmethyl)(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)acetic acidYield 63.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 90 mg of ethyl((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)acetate in 0.2 mL of methanol and 1 mL of tetrahydrofuran, 0.2 mL of a 10% aqueous sodium hydroxide solution was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with a 1 mol/L aqueous hydrochloric acid solution and neutralized, and the solvent was distilled off under reduced pressure. The resultant residue was purified by a resin; HP-20, made by Mitsubishi Chemical Corporation and an eluent of acetone to obtain 54 mg of ((2,3-dihydro(1,4)dioxino(2,3-c) pyridin-7-ylmethyl)(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)acetic acid as a light yellow solid.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe resultant residue was purified by a resin

Sources & evidence

ORD record
ord-28fa617bdd604d03a1ebc91ea771718d
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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