Sodium Hydroxide → 3-(3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoic acid

HRID 2383444Notes

Reaction equation

HRID 2383444 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][N:17]([C:21]([NH:23][C:24]5[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=5)[C:27]([O:29]CC)=[O:28])=[O:22])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][N:17]([C:21]([NH:23][C:24]5[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=5)[C:27]([OH:29])=[O:28])=[O:22])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59490753ethyl 3-(3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoate

Product 1

HCID 594904523-(3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoic acidYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoate (0.162 g, 0.33 mmol) in methanol (5 mL) was added aqueous NaOH (0.13 g in 3 mL H2O, 3.3 mmol). The reaction was stirred at room temperature for 16 hours. On completion of the reaction the solvent was removed and the resulting aqueous solution was acidified to pH<2 using 2N HCl. A solid precipitated out, which was filtered, washed with water and dried to give the desired product, 3-(3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoic acid (0.136 g, 90%) as a pale yellow solid. M.p.>136° C.; 1H NMR (400 MHz, DMSO-d6) δ12.95 (s, 1H), 8.93 (s, 1H), 8.41 (s, 1H), 8.19 (s, 1H), 8.10 (m, 1H), 7.78 (m, 1H), 7.53 (m, 1H), 7.36 (dd, J1=J2=8.4 Hz, 1H), 7.18 (m, 2H), 6.84 (m, 2H), 4.86 (m, s, 2H), 3.85 (t, J=6.0 Hz, 2H), 3.68 (s, 3H), 3.50 (m, 2H), 3.16 (t, J=6.0 Hz, 2H); LCMS [M+H]: 458.

Workup

  1. customOn completion of the reaction the solvent
  2. customwas removed
  3. customA solid precipitated out
  4. filtrationwhich was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-d962f3e4f46d47e9af9efe08dae7e654
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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