Ethanol → 5-Isothiazol-5-yl-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

HRID 1888921Notes

Reaction equation

HRID 1888921 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH:12]=[C:13]([C:15](=[S:21])[CH:16]=[CH:17][N:18](C)C)[CH:14]=1)=[O:8])[CH3:5].C(O)C.CO.OOS(N)(=O)=O>N1C=CC=CC=1>[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH:12]=[C:13]([C:15]2[S:21][N:18]=[CH:17][CH:16]=2)[CH:14]=1)=[O:8])[CH3:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 16204977hydroxyl-amine-O-sulfonic acidHCID 722974795-(3-Dimethylamino-thioacryloyl)-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

Product 1

HCID 251695065-Isothiazol-5-yl-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amideYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 0° C. solution of 5-(3-dimethylamino-thioacryloyl)-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (200 mg, 0.505 mmol) in a mixture of pyridine (80 uL), ethanol (3 mL) and MeOH (1 mL) was added hydroxyl-amine-O-sulfonic acid (0.76 mmol, 85.7 mg) in one portion. The reaction mixture was stirred for two hours, during which time the mixture was allowed to warm to room temperature. Solvent was removed in vacuo, and the residue was subjected to Preparative HPLC for separation to give 92 mg (50%) of 5-isothiazol-5-yl-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide, MS (M+H)=367.

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue was subjected to Preparative HPLC for separation

Sources & evidence

ORD record
ord-a7a8013db34346b5bde672ae00abe496
Source dataset
uspto-grants-2013_08
Patent number
US08501933B2

Reaction notes

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