Sodium Hydroxide → 1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylic acid

HRID 2193169

Reaction equation

HRID 2193169 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]3[CH2:17][CH2:16][C:15]([CH2:23][CH2:24][CH2:25][N:26]4[C:35]5[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=5)[CH:29]=[CH:28][C:27]4=[O:38])([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]3[CH2:17][CH2:16][C:15]([CH2:23][CH2:24][CH2:25][N:26]4[C:35]5[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=5)[CH:29]=[CH:28][C:27]4=[O:38])([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 59398233ethyl 1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

Product 1

HCID 593983111-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylic acidYield 14.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1 mL of an ethanol solution containing 80 mg of ethyl 1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 0.25 mL of 20% aqueous sodium hydroxide solution was added and refluxed with heating for 7.5 hours. Further, 0.30 mL of 20% aqueous sodium hydroxide solution was added and left to stand at room temperature overnight. The solvent was removed under reduced pressure, water was added, and adjusted to pH 6.5 with 6.0 mol/L hydrochloric acid. The resulting solid was filtered to give 11 mg of 1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylic acid as a white solid. Also, the filtrate was removed under reduced pressure, and the residue thus obtained was purified by reversed-phase silica gel column chromatography [eluent; acetonitrile:water=2:8] to give 31 mg of 1-(2,3-dihydro(1,4)dioxino (2,3-c)pyridin-7-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylic acid.

Workup

  1. additionwas added
  2. temperaturerefluxed
  3. temperaturewith heating for 7.5 hours
  4. waitleft
  5. customThe solvent was removed under reduced pressure, water
  6. additionwas added
  7. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-714f655b3b6f4e838f8b8d315e600c94
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Linked notes

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