Sodium Hydroxide → HCID 10091127, compound

HRID 2376633Notes

Reaction equation

HRID 2376633 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[C:14]3[C:19](=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([S:28][CH3:29])[CH:23]=4)[N:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C1COCC1>[CH3:29][S:28][C:24]1[CH:23]=[C:22]([C:20]2[N:21]=[C:12]([N:9]3[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]3)[CH:13]=[C:14]3[C:19]=2[N:18]=[CH:17][CH:16]=[CH:15]3)[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69207088HCID 69207088, compound

Product 1

HCID 10091127HCID 10091127, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[8-(3-Methylsulfanyl-phenyl)-[1,7]naphthyridin-6-yl]-piperidine-4-carboxylic acid ethyl ester (134 mg, 0.33 mmol) in THF (1 ml) is added sodium hydroxide (0.33 ml of a 1M aqueous solution). The solution is stirred at room temperature for 23 hours and then partitioned between ethyl acetate and water. The aqueous extract is acidified with 7 M HCl to pH 4 and washed with ethyl acetate (3×). The combined organic layers are then concentrated to give the title compound as an amorphous solid. MS (TOF ES+) 380.1107

Workup

  1. custompartitioned between ethyl acetate and water
  2. extractionThe aqueous extract
  3. washwashed with ethyl acetate (3×)
  4. concentrationThe combined organic layers are then concentrated

Sources & evidence

ORD record
ord-86f7b16d336e424d8c77a1472e9af7e1
Source dataset
uspto-grants-2008_12
Patent number
US07468370B2

Reaction notes

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