Methylamine → 4-tert-Butyl-N-[4-chloro-2-(5-isopropoxymethyl-4-methyl-4H-[1,2,4]triazol-3-yl)-phenyl]-benzenesulfonamide

HRID 448107Notes

Reaction equation

HRID 448107 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[C:22]2O[C:24]([CH2:27][O:28][CH:29]([CH3:31])[CH3:30])=[N:25][N:26]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:32][NH2:33]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[C:22]2[N:33]([CH3:32])[C:24]([CH2:27][O:28][CH:29]([CH3:30])[CH3:31])=[N:25][N:26]=2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 669052774-tert-butyl-N-[4-chloro-2-(5-isopropoxymethyl-[1,3,4]oxadiazol-2-yl)-phenyl]-benzenesulfonamide

Product 1

HCID 593029824-tert-Butyl-N-[4-chloro-2-(5-isopropoxymethyl-4-methyl-4H-[1,2,4]triazol-3-yl)-phenyl]-benzenesulfonamide

Procedure

In a pressure vessel, 4-tert-butyl-N-[4-chloro-2-(5-isopropoxymethyl-[1,3,4]oxadiazol-2-yl)-phenyl]-benzenesulfonamide (71 mg, 0.15 mmol) and methyl amine (40% in H2O, 1.5 mL, 0.6 mmol) were heated at 135° C. for 18 h. The reaction was cooled to room temperature, concentrated in vacuo, and the residue purified by flash column chromatography (0-50% ethyl acetate in hexane) to yield the title compound as a white solid: MS (ES) M+H expected 477.2, found 477.1.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue purified by flash column chromatography (0-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4ce1a47993ed490382a24cc836364320
Source dataset
uspto-grants-2013_07
Patent number
US08481579B2

Reaction notes

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