Sodium Hydroxide → HCID 57671621, compound

HRID 553522Notes

Reaction equation

HRID 553522 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][CH:16]=2)[N:13]([CH3:17])[C:12](=[O:18])[C:11]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])=[C:10]3[OH:26])[CH2:3][CH2:2]1.[OH-].[Na+]>CO.[Pd]>[OH:26][C:10]1[C:9]2[C:14](=[N:15][CH:16]=[C:7]([CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:8]=2)[N:13]([CH3:17])[C:12](=[O:18])[C:11]=1[C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57671555HCID 57671555, compound

Product 1

HCID 57671621HCID 57671621, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 2-(6-(3,6-dihydro-2 H-pyran-4-yl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamido)acetic acid (71 mg, 198 μmol, Example 260)) and 1 N sodium hydroxide (988 μl, 988 μmol) in MeOH (5 mL) was treated with 10% Pd/C (5.3 mg, 49 μmol) under nitrogen atmosphere. The reaction vessel was degassed and backfilled with hydrogen (3×), and the mixture was stirred at 23° C. for 75 minutes under hydrogen atmosphere. The reaction mixture was filtered from the catalyst through a pad of Celite®, and the filter cake was washed with MeOH (50 mL). The combined filtrate was concentrated and acidified with concentrated HCl. The precipitated solid was collected by filtration, washed with water (10 mL), and dried in vacuo to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 362 (M+1). 1NMR (400 MHz, DMSO-d6) δ ppm: 10.49 (s, 1 H), 8.80 (d, J=2.0 Hz, 1 H), 8.26 (d, J=1.8 Hz, 1 H), 4.14 (d, J=5.3 Hz, 1 H), 3.98 (d, J=10.4 Hz, 2 H), 3.69 (s, 3 H), 3.42-3.52 (m, 2 H), 2.91-3.09 (m, 1 H), 1.65-1.88 (m, 4H).

Workup

  1. customThe reaction vessel was degassed
  2. filtrationThe reaction mixture was filtered from the catalyst through a pad of Celite®
  3. washthe filter cake was washed with MeOH (50 mL)
  4. concentrationThe combined filtrate was concentrated
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water (10 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-ef92cd6dab0e4c6b848c09215a843663
Source dataset
uspto-grants-2011_11
Patent number
US08048892B2

Reaction notes

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