1-(propan-2-yl)-1H-pyrazol-5-amine → HCID 67124442, compound

HRID 476085

Reaction equation

HRID 476085 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][CH:18]([N:20]1[C:24]([NH2:25])=[CH:23][CH:22]=[N:21]1)[CH3:19]>C1C=CC=CC=1>[CH3:17][CH:18]([N:20]1[C:24]2[N:25]=[C:9]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)[CH:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:23]=2[CH:22]=[N:21]1)[CH3:19]

Participants

4

Reactant 2

HCID 10903411-(propan-2-yl)-1H-pyrazol-5-amineHCID 23005473Ethyl α,γ-dioxo-4-pyridinebutanoate

Product 1

HCID 67124442HCID 67124442, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
62 °C

Procedure

To a suspension of ethyl 2,4-dioxo-4-(4-pyridinyl)butanoate (442 mg, 1.997 mmol) in benzene (5 mL) was added 1-(1-methylethyl)-1H-pyrazol-5-amine (250 mg, 1.997 mmol), and the reaction mixture was stirred at 62° C. overnight. The reaction mixture was concentrated in vacuo and the residue was purified using column chromatography (Silica gel, 0 to 100% EtOAc/hexanes) to give 270 mg (43%) of product. LCMS E-S (M+H)=311.3 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.54 (t, J=7.2 Hz, 3H), 1.68 (d, J=6.6 Hz, 6H), 4.58 (q, J=7.1 Hz, 2H), 5.41-5.60 (m, 1H), 8.04-8.19 (m, 2H), 8.29 (s, 1H), 8.44-8.55 (m, 2H), 8.76-8.91 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified

Sources & evidence

ORD record
ord-eab103bea090450088cc165dce6ae519
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Linked notes

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