Hydrochloric Acid → HCID 24947966, compound

HRID 1803587Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21]([Cl:25])=[N:20][N:19]=[C:18]3Cl)=[O:14])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+].[O:29]1CCOCC1.Cl>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21]([Cl:25])=[N:20][NH:19][C:18]3=[O:29])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1,4-dichloro-phthalazine-6-carboxylic acid (3-furan-2-yl-phenyl)-amide (400 mg, 1.041 mmol), 2N NaOH (5.2 mL, 10.41 mmol) and dioxane (5 mL) was heated to 50° C. for 5 h. The reaction was diluted with water, acidified with conc. HCl to ˜pH 6. The reaction mixture was concentrated to low volume and filtered through celite. Chromatography (Hex/EtOAc) afforded 1-chloro-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid (3-furan-2-yl-phenyl)-amide (43 mg) as a pale yellow solid, 1H NMR (400 MHz, d6-DMSO) δ: 6.76 (m, 1H), 7.08 (d, 1H), 7.58 (t, 1H), 7.64 (m, 1H), 7.90 (m, 2H), 8.30 (d, 1H), 8.34 (s, 1H), 8.70 (dd, 1H), 9.05 (s, 1H), 10.98 (s, 1H), 13.19 (s, 1H) ppm; m/z (M+1) 365.90; and 4-chloro-1-oxo-1,2-dihydro-phthalazine-6-carboxylic acid (3-furan-2-yl-phenyl)-amide (40 mg) as a pale yellow solid. 1H NMR (400 MHz, d6-DMSO) δ: 6.62 (m, 1H), 6.92 (d, 1H), 7.44 (t, 1H), 7.50 (m, 1H), 7.74 (m, 1H), 7.78 (s, 1H), 8.17 (m, 1H), 8.45 (m, 2H), 8.52 (s, 1H), 10.80 (s, 1H), 13.01 (s, 1H) ppm; m/z (M+1) 365.97.

Workup

concentrationThe reaction mixture was concentrated to low volume
filtrationfiltered through celite

Sources & evidence

ORD record: ord-024cfd9f37514315823503dac41e8cf8
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349836B2

Reaction notes

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