1-Cyclopentyl-3-methyl-1H-pyrazol-5-amine → ethyl 1-cyclopentyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 476042Notes

Reaction equation

HRID 476042 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[CH:9][C:8]([CH3:12])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:13]1([C:16](=O)[CH2:17][C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1>C1C=CC=CC=1>[CH:1]1([N:6]2[C:10]3[N:11]=[C:16]([CH:13]4[CH2:14][CH2:15]4)[CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:9]=3[C:8]([CH3:12])=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 31525241-Cyclopentyl-3-methyl-1H-pyrazol-5-amineHCID 16779961Ethyl 4-cyclopropyl-2,4-dioxobutanoate

Product 1

HCID 67124342ethyl 1-cyclopentyl-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-cyclopentyl-3-methyl-1H-pyrazol-5-amine (570 mg, 3.45 mmol), ethyl 4-cyclopropyl-2,4-dioxobutanoate (635 mg, 3.45 mmol), and benzene (50 mL) wherein the reaction time was 4 h. The crude product was purified via silica gel chromatography (eluent: 0 to 10% EtOAc:Hex). The final product was collected as 0.740 g (68%). LCMS E-S (M+H)=314.3 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.04-1.21 (m, 4H) 1.47 (t, J=7.20 Hz, 3H) 1.73 (br. s., 2H) 2.00 (d, J=2.78 Hz, 2H) 2.08-2.16 (m, 4H) 2.21 (s, 1H) 2.67 (s, 3H) 4.49 (q, J=7.16 Hz, 2H) 5.32 (t, J=7.83 Hz, 1H) 7.40 (s, 1H).

Workup

  1. customThe crude product was purified via silica gel chromatography (eluent: 0 to 10% EtOAc:Hex)
  2. customThe final product was collected as 0.740 g (68%)

Sources & evidence

ORD record
ord-9e5e853aca864b0c80e16e019b6170d1
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

Loading…