Ethyl 4-cyclopropyl-2,4-dioxobutanoate → Ethyl 1-cyclobutyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 476041Notes

Reaction equation

HRID 476041 reaction equation
[CH:1]1([N:5]2[C:9]([NH2:10])=[CH:8][C:7]([CH3:11])=[N:6]2)[CH2:4][CH2:3][CH2:2]1.[CH:12]1([C:15](=O)[CH2:16][C:17](=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1>C1C=CC=CC=1>[CH:1]1([N:5]2[C:9]3[N:10]=[C:15]([CH:12]4[CH2:13][CH2:14]4)[CH:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:8]=3[C:7]([CH3:11])=[N:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 16779961Ethyl 4-cyclopropyl-2,4-dioxobutanoateHCID 566043711-Cyclobutyl-3-methyl-1H-pyrazol-5-amine

Product 1

HCID 68079207Ethyl 1-cyclobutyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The title compound was prepared in the same manner as described for intermediate 33 using 1-cyclobutyl-3-methyl-1H-pyrazol-5-amine (400 mg, 2.65 mmol), ethyl 4-cyclopropyl-2,4-dioxobutanoate (487 mg, 2.65 mmol) and benzene (50 mL), wherein the reaction time was 4 h. The final product was collected as 0.556 g (70%). LCMS E-S (M+H)=300.6 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.02-1.22 (m, 4H) 1.47 (t, J=7.07 Hz, 3H) 1.80-2.01 (m, 2H) 2.15-2.28 (m, 1H) 2.38-2.51 (m, 2H) 2.70 (s, 3H) 2.82 (td, J=9.85, 2.53 Hz, 2H) 4.49 (q, J=7.07 Hz, 2H) 5.32-5.57 (m, 1H) 7.41 (s, 1H).

Workup

  1. customThe final product was collected as 0.556 g (70%)

Sources & evidence

ORD record
ord-84046a138be04c7b80c977f2e9783761
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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