HCID 71529254, compound → HCID 71529256, compound

HRID 1770637Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:30]([F:33])([F:32])[F:31])[O:13][N:12]=[C:11]([C:14]3[CH:26]=[CH:25][C:17]([C:18]([NH:20][CH:21]4[CH2:24][S:23][CH2:22]4)=[O:19])=[C:16]([N+:27]([O-])=O)[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1>C(O)(C)C.C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:30]([F:31])([F:33])[F:32])[O:13][N:12]=[C:11]([C:14]3[CH:26]=[CH:25][C:17]([C:18]([NH:20][CH:21]4[CH2:22][S:23][CH2:24]4)=[O:19])=[C:16]([NH2:27])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4H-isoxazol-3-yl]-2-nitro-N-(thietan-3-yl)benzamide (40 mg, 0.07 mmol) and iron powder (26 mg) in isopropanol (10 ml) and acetic acid (1 ml) was heated at 70° C. for 3 hours. Isopropanol was evaporated and the residue was treated with water (10 ml) and extracted with dichloromethane (25 ml). The combined organic layers were dried over sodium sulfate, concentrated, and purified by column chromatography (hexane/ethyl acetate as eluent) to give 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4H-isoxazol-3-yl]-2-amino-N-(thietan-3-yl)benzamide (15 mg). 1H-NMR (400 MHz, CDCl3): 7.49 (2H, d), 7.42 (1H, m), 7.34 (1H, d), 6.92-6.94 (2H, m), 6.48 (1H, d) 5.18-5.20 (1H, m), 4.03 (1H, d), 3.64 (1H, d), 3.31-3.41 (4H, m), 0.82 (3H, m) ppm.

Workup

customIsopropanol was evaporated
additionthe residue was treated with water (10 ml)
extractionextracted with dichloromethane (25 ml)
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated
custompurified by column chromatography (hexane/ethyl acetate as eluent)

Sources & evidence

ORD record: ord-4f42165367c1451aa83de84f278642e1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09247740B2

Reaction notes

Loading…