1H-Indazol-5-amine → 3-(2-furanyl)-N-1H-indazol-5-yl-3-oxopropanamide

HRID 227691Notes

Reaction equation

HRID 227691 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8][C:9]([O:11]CC)=O)=[O:7].[NH2:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[CH:18]2>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:7])[CH2:8][C:9]([NH:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[CH:18]2)=[O:11]

Participants

3

Reactant 2

HCID 880121H-Indazol-5-amineHCID 2759240Ethyl 3-(fur-2-yl)-3-oxopropanoate

Product 1

HCID 577559153-(2-furanyl)-N-1H-indazol-5-yl-3-oxopropanamide

Conditions

Temperature
180 °C

Procedure

Ethyl 2-(fur-2-oyl)acetate (3 mL) was mixed with 5-aminoindazole (0.50 g) and heated in a SmithSynthesizer to 180° C. for 300 seconds. The crude mixture was then purified by silica gel chromatography to yield the title compound as a light purple solid. 1H NMR (keto tautomer) (400 MHz, DMSO-D6) δ ppm 12.99 (s, 1H), 10.22 (s, 1H), 8.11 (s, 1H), 8.05 (s, 1H), 8.02 (s, 1H), 7.58 (d, 1H), 7.49 (d, 1H), 7.40 (dd, 1H), 6.77 (dd, 1H), 3.96 (s, 2H). MS m/z 270 (M+1)+.

Workup

  1. customThe crude mixture was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-f9730e71b5524dfba0d8830683e9c443
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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