Hydrochloric Acid → HCID 24947968, compound

HRID 1667501Notes

Reaction equation

[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=2[NH:17][C:18]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[C:26]([Cl:30])=[N:25][N:24]=[C:23]3Cl)=[O:19])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+].[O:34]1CCOCC1.Cl>O>[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=2[NH:17][C:18]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[C:26]([Cl:30])=[N:25][NH:24][C:23]3=[O:34])=[O:19])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1,4-dichloro-phthalazine-6-carboxylic acid (2-morpholin-4-yl-5-trifluoromethyl-phenyl)-amide (322 mg, 0.683 mmol), 2N NaOH (3.4 mL, 6.83 mmol) and dioxane (5 mL) was heated to 50° C. for 1 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 (2-morpholin-4-yl-5-trifluoromethyl-phenyl)-amide (49 mg) as a yellow solid, 1H NMR (400 MHz, d6-DMSO) δ: 2.99 (m, 4H), 3.80 (m, 4H), 7.41 (d, 1H), 7.56 (dd, 1H), 8.18 (d, 1H), 8.28 (s, 1H), 8.51 (dd, 1H), 8.80 (d, 1H), 10.23 (s, 1H), 13.05 (s, 1H) ppm; m/z (M+1) 452.96; and 4-chloro-1-oxo-1,2-dihydro-phthalazine-6-carboxylic acid (2-morpholin-4-yl-5-trifluoromethyl-phenyl)-amide (40 mg) as a pale yellow solid. 1H NMR (400 MHz, d6-DMSO) δ: 2.99 (m, 4H), 3.80 (m, 4H), 7.41 (d, 1H), 7.58 (dd, 1H), 8.29 (s, 1H), 8.43 (s, 2H), 8.46 (s, 1H), 10.23 (s, 1H), 13.02 (s, 1H) ppm; m/z (M+1) 452.96.

Workup

concentrationThe reaction mixture was concentrated to low volume
filtrationfiltered through celite

Sources & evidence

ORD record: ord-26129e75296549539a068cfc6bf9be8f
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044041B2

Reaction notes

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