Sodium Hydroxide → 6-Cyclopropyl-1-(1-cyclopropylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522451Notes

Reaction equation

[CH:1]1([C:4]2[CH:5]=[C:6]([C:19]([O:21]CC)=[O:20])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]([CH:16]4[CH2:18][CH2:17]4)[CH3:15])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CCO>[CH:1]1([C:4]2[CH:5]=[C:6]([C:19]([OH:21])=[O:20])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]([CH:16]4[CH2:17][CH2:18]4)[CH3:15])[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

To an EtOH (10 mL) solution of ethyl 6-cyclopropyl-1-(1-cyclopropylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (720 mg, 2.297 mmol) was added sodium hydroxide (6.89 mL, 6.89 mmol) and the mixture heated at 70° C. for 1 hour. The solvent was removed in vacuo and the residue was dissolved in 20 mL of water. The contents were acidifed with acetic acid, and extracted with EtOAc (4×30 mL). The combined organic extracts were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The final product was collected as a solid, 0.560 g (85%). LCMS E-S (M+H)=286.3 1H NMR (400 MHz, DMSO-d6) δ ppm 0.15-0.33 (m, 2 H), 0.38 (dq, J=9.57, 4.89 Hz, 1 H), 0.50-0.65 (m, 1 H), 0.90-1.10 (m, 4 H), 1.27-1.42 (m, 1 H), 1.57 (d, J=6.82 Hz, 3 H), 2.23-2.36 (m, 1 H), 2.57 (s, 3 H), 4.18 (dq, J=9.32, 6.83 Hz, 1 H), 7.44 (s, 1 H), 12.79 (br. s., 1 H).

Workup

customThe solvent was removed in vacuo
dissolutionthe residue was dissolved in 20 mL of water
extractionextracted with EtOAc (4×30 mL)
washThe combined organic extracts were washed with water, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe final product was collected as a solid, 0.560 g (85%)

Sources & evidence

ORD record: ord-dc22062366734463a982276b151a17d9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073924B2

Reaction notes

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