Hydrochloric Acid → HCID 24948725, compound

HRID 1803546Notes

Reaction equation

[F:1][CH:2]([F:25])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C:19]([Cl:23])=[N:18][N:17]=[C:16]3Cl)=[O:12])[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+].[O:28]1CCOCC1.Cl>O>[F:1][CH:2]([F:25])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C:19]([Cl:23])=[N:18][NH:17][C:16]3=[O:28])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1,4-dichloro-phthalazine-6-carboxylic acid (3-difluoromethoxy-phenyl)-amide (0.26 g, 0.68 mmol), 2N NaOH (3.4 mL, 6.8 mmol) and dioxane (4 mL) was heated to 50° C. for 2 hours. The reaction was diluted with water, acidified with conc. HCl to ˜pH 4 and extracted with EtOAc (×3). The combined organic phase was washed with brine, dried (Na2SO4) and concentrated. Chromatography (Hex/EtOAc) afforded 1-chloro-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid (3-difluoromethoxy-phenyl)-amide (60 mg), 1H-NMR (DMSO-d6) δ: 13.02 (s, 1H), 10.88 (s, 1H), 8.88 (d, 1H), 8.52 (dd, 1H), 8.14 (d, 1H), 7.75 (m, 1H), 7.69 (m, 1H), 7.43 (m, 1H), 7.23 (t, 1H), 6.96 (dd, 1H). m/z (M+H)=366; and 4-chloro-1-oxo-1,2-dihydro-phthalazine-6-carboxylic acid (3-difluoromethoxy-phenyl)-amide (39 mg), 1H-NMR (DMSO-d6) δ: 12.85 (s, 1H), 10.87 (s, 1H), 8.47 (m, 1H), 8.42 (m, 2H), 7.73 (m, 1H), 7.65 (m, 1H), 7.44 (m, 1H), 7.23 (t, 1H), 6.96 (dd, 1H). m/z (M+H)=366.

Workup

extractionextracted with EtOAc (×3)
washThe combined organic phase was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-78de773a518b4bfebf60dfa9c554c747
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349836B2

Reaction notes

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