N-(3-Aminophenyl)methanesulfamide → HCID 71060627, compound

HRID 537869Notes

Reaction equation

HRID 537869 reaction equation
Cl[C:2]1[O:3][C:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([F:15])[CH:8]=2)=[CH:5][N:6]=1.[NH2:16][C:17]1[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=1>CC(O)C>[C:11]([C:10]1[CH:13]=[CH:14][C:7]([C:4]2[O:3][C:2]([NH:16][C:17]3[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=3)=[N:6][CH:5]=2)=[CH:8][C:9]=1[F:15])#[N:12]

Participants

4

Reactant 2

HCID 2734262N-(3-Aminophenyl)methanesulfamideHCID 71060236HCID 71060236, compound

Product 1

HCID 71060627HCID 71060627, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(2-chlorooxazol-5-yl)-2-fluorobenzonitrile 39 (0.225 g, 1.01 mmol) and commercially available N-(3-aminophenyl)methanesulfonamide 6 (0.188 g, 1.01 mmol) in 2-propanol (20 mL) was heated to 80° C. for 18 h with stirring. Reaction mixture was evaporated and crude product was purified using MPLC (Biotage) silica column (Biotage) (Acetone/hexane as an eluent) to provide N-(3-((5-(4-cyano-3-fluorophenyl)oxazol-2-yl)amino)phenyl)methane sulfonamide 40 (0.319 g, 84% yield) as a solid. MS (ES) m/z 373 (M+H+).

Workup

  1. customReaction mixture
  2. customwas evaporated
  3. customcrude product was purified

Sources & evidence

ORD record
ord-124e0aa7673942059381e54ca13ff6c7
Source dataset
uspto-grants-2014_10
Patent number
US08865709B2

Reaction notes

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