Hydrochloric Acid → 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylacetic acid

HRID 2383478Notes

Reaction equation

HRID 2383478 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][N:17]([CH:21]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:22]([O:24]CC)=[O:23])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[OH-].[Na+].Cl>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]([CH:21]([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)[C:22]([OH:24])=[O:23])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59490451ethyl 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylacetate

Product 1

HCID 594907752-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylacetate (0.116 g, 0.25 mmol) in methanol (3 mL) was added 1.5 M NaOH (1.67 mL, 2.5 mmol). The reaction mixture was stirred at room temperature for 16 hours. The reaction was then acidified to pH 2-3 using 1N HCl. The mixture was then extracted with dichloromethane (3×20 mL). The organic extracts were combined, dried (Na2SO4), filtered and concentrated under reduced pressure to afford the pure desired product 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylacetic acid as an off-white solid; (0.095 g, 87%). M.p. 130-145° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.34 (s, 1H), 8.17 (s, 1H), 7.53 (m, 5H), 7.18 (m, 2H), 6.84 (m, 2H), 5.57 (s, 2H), 4.85 (m, 1H), 4.05 (m, 2H), 3.68 (s, 3H), 3.21 (m, 4H); LCMS [M+H]: 429.

Workup

  1. extractionThe mixture was then extracted with dichloromethane (3×20 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-17a2a5a15f43494b830e5d4c6e4e8f80
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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