1-Isopropyl-3-methyl-1H-pyrazol-5-amine → Ethyl 3-methyl-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 1522487Notes

Reaction equation

HRID 1522487 reaction equation
O=[C:2]([CH2:8][C:9](=O)[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:17][C:18]1[CH:22]=[C:21]([NH2:23])[N:20]([CH:24]([CH3:26])[CH3:25])[N:19]=1>C1C=CC=CC=1>[CH3:17][C:18]1[C:22]2[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:8][C:9]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[N:23][C:21]=2[N:20]([CH:24]([CH3:26])[CH3:25])[N:19]=1

Participants

4

Reactant 2

HCID 1210181-Isopropyl-3-methyl-1H-pyrazol-5-amineHCID 23005473Ethyl 2,4-dioxo-4-(pyridin-4-yl)butanoate

Product 1

HCID 67124410Ethyl 3-methyl-1-(1-methylethyl)-6-(4-pyridinyl)-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 64 using ethyl 2,4-dioxo-4-(4-pyridinyl)butanoate (766 mg, 2.87 mmol), benzene (6 mL), and 3-methyl-1-(1-methylethyl)-1H-pyrazol-5-amine (400 mg, 2.87 mmol). The crude product was purified using column chromatography (Silica gel, eluent: 0 to 30% MeOH/DCM) to give 95 mg (10%) of product. LCMS E-S (M+H)=325.3. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.48-1.56 (m, 3 H), 1.61-1.73 (m, 6 H), 2.77 (s, 3 H), 4.56 (q, J=7.2 Hz, 2 H), 5.37-5.50 (m, 1 H), 8.02-8.16 (m, 3 H), 8.76-8.83 (m, 2 H).

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-a056193faa7343a099097c1f21fdb7a6
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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