Water → HCID 86691632, compound

HRID 624322Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([C:25]4[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([CH:34]=4)[C:30]([O:32]C)=[O:31])=[CH:18][C:11]=3[C:12]=2[C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)=[CH:4][CH:3]=1.O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([C:25]4[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([CH:34]=4)[C:30]([OH:32])=[O:31])=[CH:18][C:11]=3[C:12]=2[C:13]2[NH:17][CH:16]=[CH:15][N:14]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of methyl 5-(2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoate (370 mg, 0.759 mmol) in a mixture of THF (40 mL)/water (4 mL) at room temperature was added a 2.0 M aqueous sodium hydroxide solution (1.518 mL, 3.04 mmol). The reaction mixture was heated to 50° C. and maintained at the same temperature overnight. The reaction mixture was concentrated to remove the solvent. The residue was diluted with water, acidified by using 1.5 N HCl, filtered and dried under suction to give the title compound as a yellow solid. Yield: 320 mg (89%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 13.11-13.73 (m, 1H) 12.66-12.97 (m, 1H) 8.53 (s, 1H) 7.94-8.09 (m, 2H) 7.63-7.82 (m, 1H) 7.34-7.51 (m, 5H) 7.23 (d, J=8.78 Hz, 2H) 3.88 (s, 3H). LCMS: (ES+) m/z=474.23 (M+H)+; Column—ACQUITY UPLC BEH C8 (50×2.1 mm; 1.7 nm); Mphase A: 5 mM Ammonium Acetate:MeCN (95:5); Mphase B: 5 mM Ammonium Acetate:MeCN (5:95)

Workup

temperaturemaintained at the same temperature overnight
concentrationThe reaction mixture was concentrated
customto remove the solvent
additionThe residue was diluted with water
filtrationfiltered
customdried under suction

Sources & evidence

ORD record: ord-4102a28cac174df2a2d0b2417e3b26da
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303020B2

Reaction notes

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