Acetic Acid → HCID 89761947, compound

HRID 528522Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:22]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=2[O:37][CH3:38])[C:23]2[S:27][N:26]=[CH:25][N:24]=2)(=[O:21])=[O:20])=[CH:15][C:14]=1[N+:39]([O-])=O.C1COCC1.C(O)(=O)C>C(Cl)Cl.CO.[Fe]>[NH2:39][C:14]1[CH:15]=[C:16]([S:19]([N:22]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=2[O:37][CH3:38])[C:23]2[S:27][N:26]=[CH:25][N:24]=2)(=[O:21])=[O:20])[CH:17]=[CH:18][C:13]=1[NH:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:7][C:2]=1[Cl:1]

Participants

Conditions

Temperature: 70 °C

Procedure

A vial was charged with INTERMEDIATE T (0.250 g, 0.397 mmol), iron (0.222 g, 3.97 mmol), THF (0.25 mL), and acetic acid (0.25 mL). The vial was sealed and stirred at 70° C. for one hour. The mixture was diluted with DCM and MeOH, then filtered through a pad of Celite® (diatomaceous earth) and concentrated. The material was purified via silica gel chromatography (40 g, gradient elution 0 to 50% EtOAc:Heptane) to afford 3-amino-4-((2-chloro-4-(trifluoromethyl)phenyl)amino)-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (INTERMEDIATE U) as an off-white solid. m/z (ESI) 621.8 (M+Na)+.

Workup

customThe vial was sealed
filtrationfiltered through a pad of Celite® (diatomaceous earth)
concentrationconcentrated
customThe material was purified via silica gel chromatography (40 g, gradient elution 0 to 50% EtOAc:Heptane)

Sources & evidence

ORD record: ord-4136126eb5db404381096f9f781a8799
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346798B2

Reaction notes

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