Trifluoromethanesulfonyl chloride → HCID 22141247, compound

HRID 428865Notes

Reaction equation

HRID 428865 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:28])([F:27])[S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[F:21][C:22]([F:28])([F:27])[S:23]([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:25])=[O:24]

Participants

5

Reactant 2

HCID 79000Trifluoromethanesulfonyl chlorideHCID 221413223-(3-Hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine

Product 1

HCID 22141247HCID 22141247, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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 (10 ml) cooled at 0° C. was treated with trifluoromethanesulphonyl chloride (0.14 g, 0.88 rumol) and 4-dimethylaminopyridine (5 mg). The reaction mixture was stirred at room temperature for 3 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 brown solid, (17 mg, 12%).

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 brown solid, (17 mg, 12%)

Sources & evidence

ORD record
ord-8c5325bffe8b44e9bb0dec45b0de63a8
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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