Triethylamine → N-{3-[1-(4-Cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethylamino]-propyl}-3-hydroxy-benzenesulfonamide

HRID 1060896Notes

Reaction equation

HRID 1060896 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)(=[O:8])=[O:7].[NH2:16][C:17]([C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([F:33])[CH:26]=1)([C:19]1[N:20]([CH3:24])[CH:21]=[N:22][CH:23]=1)[CH3:18].CCN(CC)CC>CC#N>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([C:17]([NH:16][CH2:2][CH2:3][CH2:4][NH:5][S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)(=[O:8])=[O:7])([C:19]2[N:20]([CH3:24])[CH:21]=[N:22][CH:23]=2)[CH3:18])=[CH:26][C:27]=1[F:33])#[N:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11470581(+)-4-[1-amino-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2-fluoro-benzonitrileHCID 18629458N-(3-bromo-propyl)-3-hydroxy-benzenesulfonamide

Product 1

HCID 70026827N-{3-[1-(4-Cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethylamino]-propyl}-3-hydroxy-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(3-Bromo-propyl)-3-hydroxy-benzenesulfonamide (0.23 g, 0.782 mmol), (+)-4-[1-amino-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2-fluoro-benzonitrile (Example 1, Step I) (0.191 g, 0.78 mmol), and Et3N (0.218 mL, 1.56 mmol) were dissolved in CH3CN (5 mL) and heated at reflux for 16 h. The reaction mixture was concentrated in vacuo, azeotroped with toluene, and dried to give the title compound. MS (M+1) 458.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customazeotroped with toluene
  5. customdried

Sources & evidence

ORD record
ord-57d6f351b74f419ca0157b8ec036bd8f
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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