Acetic Acid → 4-tert-butyl-N-[6-chloro-2-(4-ethyl-5-methyl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-benzenesulfonamide

HRID 2245839Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:16]([C:22]([NH:24][NH2:25])=O)=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:26](OC)(OC)(OC)[CH3:27].[CH2:34]([NH2:36])[CH3:35].CC(O)=O>O1CCOCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:16]([C:22]3[N:36]([CH2:34][CH3:35])[C:26]([CH3:27])=[N:25][N:24]=3)=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

A 25 mL scintillation vial was charged with 4-tert-butyl-N-(6-chloro-2-hydrazinocarbonyl-pyridin-3-yl)-benzenesulfonamide (691 mg, 1.8 mmol), trimethyl orthoacetate (0.35 mL, 2.8 mmol), ethylamine (5 mL, 2.0 M), AcOH (3.0 mL), and dioxane (10 mL). The vial was sealed, heated to 130° C., and stirred for three hours. The volatiles were then evacuated in vacuo and the residue was purified via automated silica gel chromatography and then preparative HPLC to afford 4-tert-butyl-N-[6-chloro-2-(4-ethyl-5-methyl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-benzenesulfonamide as a white powder: MS (ES) M+H expected 434.1, found 434.1.

Workup

customThe vial was sealed
customThe volatiles were then evacuated in vacuo
customthe residue was purified

Sources & evidence

ORD record: ord-0b3108ebcbaf459585043d954daff35f
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683176B2

Reaction notes

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