1-Cyclohexyl-3-methyl-1H-pyrazol-5-amine → Ethyl 1-cyclohexyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 476045Notes

Reaction equation

HRID 476045 reaction equation
[CH:1]1([N:7]2[C:11]([NH2:12])=[CH:10][C:9]([CH3:13])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:14]1([C:17](=O)[CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15]1>>[CH:1]1([N:7]2[C:11]3[N:12]=[C:17]([CH:14]4[CH2:15][CH2:16]4)[CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10]=3[C:9]([CH3:13])=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 45719511-Cyclohexyl-3-methyl-1H-pyrazol-5-amineHCID 16779961Ethyl 4-cyclopropyl-2,4-dioxobutanoate

Product 1

HCID 67124309Ethyl 1-cyclohexyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Procedure

The title compound was prepared in the same manner as described for intermediate 37 using 1-(1-cyclohexyl)-3-methyl-1H-pyrazol-5-amine (500 mg, 2.79 mmol) and ethyl 4-cyclopropyl-2,4-dioxobutanoate (514 mg, 2.79 mmol). The final product was collected as a solid, 0.827 g (91%). LCMS E-S (M+H)=328.3 1H NMR (400 MHz, DMSO-d6) δ ppm 1.01-1.10 (m, 3H), 1.20-1.30 (m, 1H), 1.37 (t, J=7.07 Hz, 3H), 1.41-1.52 (m, 2H), 1.70 (d, 1H), 1.79-1.98 (m, 6H), 2.30-2.38 (m, 1H), 2.54 (s, 3H), 4.42 (q, J=7.07 Hz, 2H), 4.60-4.74 (m, 1H), 7.44 (s, 1H).

Workup

  1. customThe final product was collected as a solid, 0.827 g (91%)

Sources & evidence

ORD record
ord-93c4ba1775a64478a113ef554ad98130
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

Loading…