2,2,2-Trifluoroethanesulfonyl chloride → HCID 22141296, compound

HRID 428866Notes

Reaction equation

HRID 428866 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:21][C:22]([F:29])([F:28])[CH2:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[F:21][C:22]([F:29])([F:28])[CH2:23][S:24]([NH:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:10]2([CH3:13])[CH:11]3[CH:9]2[CH2:8][N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:12]3)[CH:15]=1)(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 221413223-(3-Hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine

Product 1

HCID 22141296HCID 22141296, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine (Preparation 12, 0.10 g, 0.37 mmol) in pyridine (8 ml) cooled at 0° C. was treated with 2,2,2-trifluoroethanesulphonyl chloride (0.08 g, 0.44 mmol). The reaction mixture was allowed to warm to room temperature and then stirred for 16 h. The reaction mixture was concentrated in vacuo and the residue was poured into saturated aqueous sodium hydrogen carbonate solution (100 ml) and extracted with dichloromethane (3×50 ml). The combined organics were dried (Na2SO4) and then concentrated in vacuo. The crude residue was purified by preparative HPLC (condition 7) to give a yellow solid, (15 mg, 10%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was poured into saturated aqueous sodium hydrogen carbonate solution (100 ml)
  3. extractionextracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative HPLC (condition 7)
  7. customto give a yellow solid, (15 mg, 10%)

Sources & evidence

ORD record
ord-75c7103e883b42388843dde2bd5285a5
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

Loading…