Sodium Hydroxide → HCID 59490683, compound

HRID 2383441Notes

Reaction equation

HRID 2383441 reaction equation
[CH:1]1[C:13]2[C:12]3[CH2:11][CH2:10][N:9]([C:14]([NH:16][C:17]4[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=4)[C:20]([O:22]CC)=[O:21])=[O:15])[CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[NH:3][N:2]=1.[OH-].[Na+]>CO>[CH:1]1[C:13]2[C:12]3[CH2:11][CH2:10][N:9]([C:14]([NH:16][C:17]4[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=4)[C:20]([OH:22])=[O:21])=[O:15])[CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[NH:3][N:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59490542HCID 59490542, compound

Product 1

HCID 59490683HCID 59490683, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoate (0.593 g, 1.62 mmol) in methanol (10 mL) was added aqueous NaOH (0.64 g in 6 mL of H2O, 16.2 mmol). The reaction was stirred at room temperature for 16 hours. The solvent was then removed under reduced pressure the resulting aqueous solution acidified to pH<2 using 2N HCl. A white precipitate crashed out, which was filtered, washed with water and dried to give the pure desired product, 3-(6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoic acid (0.539 g, 98%) as a white solid; M.p.=237-241° C.; 400 MHz 1H NMR (DMSO-d6) δ: 9.0 (s, 1H), 8.41 (s, 1H), 8.26 (s, 1H), 8.14-8.1 (m, 1H), 7.82-7.78 (m, 1H), 7.56-7.51 (m, 1H), 7.4-7.34 (m, 1H), 4.81 (s, 2H), 3.86 (t, J=6 hz, 2H), 3.18 (t, J=6 Hz, 2H); LCMS [M+H]: 338.

Workup

  1. customThe solvent was then removed under reduced pressure the resulting aqueous solution
  2. filtrationwhich was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-25b9ff9be6cb4a2c9bcdd33db9a94e4c
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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