Sodium Hydroxide → 1-(1-Methylethyl)-6-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 476079Notes

Reaction equation

[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([CH2:18][CH2:19][CH3:20])[CH:11]=[C:12]([C:13]([O:15]CC)=[O:14])[C:7]=2[CH:6]=[N:5]1)[CH3:3].[OH-].[Na+]>C(O)C.C1COCC1>[CH3:3][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([CH2:18][CH2:19][CH3:20])[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[C:7]=2[CH:6]=[N:5]1)[CH3:1]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 1-(1-methylethyl)-6-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (180 mg, 0.654 mmol) in ethanol (5 mL) and THF (1 mL) was added sodium hydroxide (1.090 mL, 3.27 mmol), and the mixture was stirred at 40° C. for 1 h. The volatiles were removed under reduced pressure. The aqueous phase was acidified to pH 3 with aq. 1N HCl. The solid precipitate formed was collected by filtration and dried under high vacuum to give 144 mg (89%) of product, which was used for next reaction without further purification. LCMS E-S (M+H)=248.1 1H NMR (400 MHz, DMSO-d6) δ ppm 0.82-1.12 (m, 3H), 1.50 (d, J=6.6 Hz, 6H), 1.78 (m, 2H), 2.80-3.11 (m, 2H), 5.09-5.38 (m, 1H), 7.47-7.72 (s, 1H), 8.18-8.46 (s, 1H), 13.82 (s, 1H).

Workup

customThe volatiles were removed under reduced pressure
customThe solid precipitate formed
filtrationwas collected by filtration
customdried under high vacuum

Sources & evidence

ORD record: ord-6198514eeff443b8b567dd2cf1656d23
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637509B2

Reaction notes

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