Urea → HCID 178428487, compound

HRID 2189160Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[C:14]3[CH3:20])=[C:4]([CH3:22])[CH:3]=1.[NH2:23][C:24]([NH2:26])=[O:25].Cl.O1CCOCC1>CCO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:26][C:24](=[O:25])[N:23]=[C:10]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[NH:16][N:15]=[C:14]4[CH3:20])[CH:9]=2)=[C:4]([CH3:22])[CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of (E)-1-(4-amino-2-methylphenyl)-3-(3-methyl-1H-indazol-5-yl)prop-2-en-1-one (0.480 g, 1.64 mmol) in EtOH (5 mL) were added urea (0.900 g, 15 mmol) and 4N HCl/dioxane (5 mL, 20 mmol). The reaction mixture was heated to 110° C. for 17 hours, cooled down and concentrated in vacuo. The product was purified by SiO2 flash chromatography (ethyl acetate to 60:40 ethyl acetate/methanol) and preparative HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate), followed by concentration in vacuo and lyophilization to afford the title compound as an acetate salt (58 mg, 11%). 1H NMR (400 MHz, d6-DMSO): δ 8.6 (s, 1H), 8.15 (d, 1H), 7.54 (d, 1H), 7.20 (d, 1H), 7.01 (s, 1H), 6.49 (m, 2H), 5.56 (s, 2H), 2.54 (s, 3H), 2.3 (s, 3H), 1.89 (s, 1H); MS (EI) for C19H17N5O: 332.3 (MH±).

Workup

temperaturecooled down
concentrationconcentrated in vacuo
customThe product was purified by SiO2 flash chromatography (ethyl acetate to 60:40 ethyl acetate/methanol) and preparative HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate)
concentrationfollowed by concentration in vacuo and lyophilization

Sources & evidence

ORD record: ord-a3f0446616784b6f8e1ee5eaa614e2a2
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324231B2

Reaction notes

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