1-(propan-2-yl)-1H-pyrazol-5-amine → Ethyl 1-(1-methylethyl)-6-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 476078Notes

Reaction equation

O=[C:2]([CH2:8][C:9](=O)[CH2:10][CH2:11][CH3:12])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:14][CH:15]([N:17]1[C:21]([NH2:22])=[CH:20][CH:19]=[N:18]1)[CH3:16]>C1C=CC=CC=1>[CH3:14][CH:15]([N:17]1[C:21]2[N:22]=[C:9]([CH2:10][CH2:11][CH3:12])[CH:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:20]=2[CH:19]=[N:18]1)[CH3:16]

Participants

Conditions

Temperature: 62 °C

Procedure

To a solution of ethyl 2,4-dioxoheptanoate (446 mg, 2.397 mmol) in benzene (5 mL) was added 1-(1-methylethyl)-1H-pyrazol-5-amine (300 mg, 2.397 mmol), and the mixture was stirred at 62° C. for 18 h. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography (Silica gel, gradient of 0 to 100% EtOAc/hexanes) to give 370 mg (56%) of product. LCMS E-S (M+H)=276.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.99-1.12 (m, 3H), 1.46-1.54 (m, 3H), 1.58-1.70 (m, 6H), 1.82-1.96 (m, 2H), 2.91-3.02 (m, 2H), 4.51 (q, J=7.2 Hz, 2H), 5.28-5.44 (m, 1H), 7.58-7.68 (s, 1H), 8.27-8.40 (s, 1H)

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe residue purified by column chromatography (Silica gel, gradient of 0 to 100% EtOAc/hexanes)

Sources & evidence

ORD record: ord-096447f75dbf4bbb861bec933930ec23
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637509B2

Reaction notes

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