4-(Methylsulfonyl)aniline → HCID 90204326, compound

HRID 927039Notes

Reaction equation

HRID 927039 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:22][S:23]([C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:30][C:29]3[CH:28]=[CH:27][C:26]([S:23]([CH3:22])(=[O:25])=[O:24])=[CH:32][CH:31]=3)=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 796174-(Methylsulfonyl)anilineHCID 5049666Sodium triacetoxyborohydrideHCID 90203282HCID 90203282, compound

Product 1

HCID 90204326HCID 90204326, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of [3-(4-formyl-phenyl)-isoxazol-4-yl]-carbamic acid tert-butyl ester (30 mg, 0.1 mmol) and 4-methanesulfonylaniline (30 mg, 0.17 mmol) in 1,2-dichloroethane (1 mL) was added sodium trisacetoxy borohydride (50 mg, 0.23 mmol). The reaction mixture was stirred for 14 h and then loaded directly on a silica gel column. Elution with 33% hexane in ethyl acetate provided (3-{4-[(4-methanesulfonyl-phenylamino)-methyl]-phenyl}-isoxazol-4-yl)-carbamic acid tert-butyl ester as a waxy solid. This was dissolved in 4M HCl in dioxane and stirred for 1 h. Removal of volatiles under reduced pressure afforded 3-{4-[(4-methanesulfonyl-phenylamino)-methyl]-phenyl}-isoxazol-4-ylamine hydrochloride as a white solid. MH+=344.3

Workup

  1. washElution with 33% hexane in ethyl acetate

Sources & evidence

ORD record
ord-9cad5ea6533d4330b4a4b15c815a36bb
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

Loading…