Sodium Hydroxide → HCID 85471029, compound

HRID 1465677Notes

Reaction equation

[CH:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[C:26]4=[N:27][O:28][C:24]5=[C:25]4[C:16]([C:17](=[O:29])[C:18]4[C:23]5=[CH:22][CH:21]=[CH:20][CH:19]=4)=[C:15]([NH:30][C:31]4[CH:39]=[CH:38][C:34]([C:35]([OH:37])=[O:36])=[CH:33][CH:32]=4)[CH:14]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+:41]>CO>[CH:1]1([N:7]2[CH2:8][CH2:9][N:10]([C:13]3[C:26]4=[N:27][O:28][C:24]5=[C:25]4[C:16]([C:17](=[O:29])[C:18]4[C:23]5=[CH:22][CH:21]=[CH:20][CH:19]=4)=[C:15]([NH:30][C:31]4[CH:32]=[CH:33][C:34]([C:35]([O-:37])=[O:36])=[CH:38][CH:39]=4)[CH:14]=3)[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[Na+:41]

Participants

Conditions

Temperature: 40 °C

Procedure

Dissolving intermediate 6, 4-((3-(4-cyclohexylpiperazin-1-yl)-6-oxo-6H-anthra[1,9-cd]isoxazol-5-yl)amino)benzoic acid in sodium hydroxide in methanol solution. Raising temperature to about 40° C. and maintaining for 2-3 hours. Then lowering temperature and filtering solid to get Compound I, sodium 4-((3-(4-cyclohexylpiperazin-1-yl)-6-oxo-6H-anthra[1,9-cd]isoxazol-5-yl)amino)benzoate. The compound was purified in sodium hydroxide in methanol solution and dried. It gave more than 99% (HPLC, area %) purity and about 45% yield. Mass spectra gave [M+1]=523.2. 1H-NMR (400 MHz, DMSO-d6, see also FIG. 3), ppm (δ): 11.79 (1H, s), 8.48 (1H, d), 8.20 (1H, d), 7.93 (2H, d), 7.84 (1H, t), 7.72 (1H, t), 7.35 (2H, d), 6.39 (1H, s), 3.85 (4H, m), 2.72-2.70 (4H, m), 2.28-2.265 (1H, m), 1.72-1.78 (4H, m), 1.55-1.58 (1H, m), 1.08-1.23 (5H, m).

Workup

temperaturemaintaining for 2-3 hours
filtrationfiltering solid

Sources & evidence

ORD record: ord-8283f41117dd4c8b9daef7ca59cafc47
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999992B2

Reaction notes

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