Butylamine → HCID 53787446, compound

HRID 274609Notes

Reaction equation

HRID 274609 reaction equation
C(O[C@@:5]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25])([C@H:12]([S:14](Cl)(=[O:16])=[O:15])[CH3:13])[CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1)(=O)C.[CH2:26]([NH2:30])[CH2:27][CH2:28][CH3:29]>ClCCl>[CH2:26]([NH:30][S:14]([C:12](=[C:5]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25])[CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1)[CH3:13])(=[O:15])=[O:16])[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 10430695HCID 10430695, compound

Product 1

HCID 53787446HCID 53787446, compoundYield 8.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (4 ml) was dissolved (2R,3R)-3-chlorosulfonyl-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butyl acetate (125 mg). To the solution was added, under ice-cooling, n-butylamine (23 mg). The reaction mixture was stirred for 20 minutes under ice-cooling, which was concentrated. The concentrate was subjected to a silica gel chromatography (eluent: hexane/ethyl acetate=1/2→ethyl acetate) for purification to give, as the first eluate, N-butyl-3- (2,4-difluorophenyl)-4-(1H-1,2,4-triazol-1-yl) -2-butene-2-sulfonamide (isomer B, Compound 33, 10 mg) as a colorless oily substance, and, as the second eluate, N-butyl-3-(2,4-difluorophenyl)-4-(1H-1, 2,4-triazol-1-yl) -2-butene-2-sulfonamide (isomer A, Compound 32, 45 mg) as a colorless solid substance.

Workup

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. temperaturecooling
  4. concentrationwhich was concentrated
  5. customThe concentrate was subjected to a silica gel chromatography (eluent: hexane/ethyl acetate=1/2→ethyl acetate) for purification

Sources & evidence

ORD record
ord-c94db2361bc1442d8bb7260cc9498ab8
Source dataset
uspto-grants-1995_02
Patent number
US05389663

Reaction notes

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