Water → HCID 22141289, compound

HRID 428875Notes

Reaction equation

HRID 428875 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2(NC2C=CC=CC=2)[CH2:13][C:14]([F:17])([F:16])[F:15])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33].O.Cl[CH2:38]Cl>>[CH2:1]([N:7]1[CH2:8][CH:9]2[CH:11]([C:10]2([C:26]2[CH:38]=[C:30]([NH:25][S:32]([CH3:31])(=[O:34])=[O:33])[CH:29]=[CH:28][CH:27]=2)[CH2:13][C:14]([F:15])([F:16])[F:17])[CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 86587192HCID 86587192, compound

Product 1

HCID 22141289HCID 22141289, compoundYield 40%

Conditions

Temperature
-12 °C

Procedure

3-[3-Hexyl-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hex-6-yl aniline (Preparation 101, 143 mg, 0.42 mmol) was dissolved in anhydrous dichloromethane (3 ml) in a dry, nitrogen-flushed flask and cooled to −12° C. in an ice/methanol bath. Pyridine (54 μl, 0.67 mmol) was added dropwise followed by methanesulfonyl chloride (39 μl, 0.50 mmol). The mixture was allowed to slowly warm to room temperature, whereupon its colour changed from yellow to bright amber. After 3 h, the mixture was treated with water (20 ml) and extracted with dichloromethane (3×20 ml). The combined organic extracts were washed with brine (20 ml), dried (MgSO4), filtered and the solvent removed in vacuo. The crude product was purified by chromatography on silica gel (5 g), eluting with hexane ether (2:1) to give the product as an amber gum (71 mg, 40%).

Workup

  1. customflushed flask
  2. temperatureto slowly warm to room temperature, whereupon its colour
  3. extractionextracted with dichloromethane (3×20 ml)
  4. washThe combined organic extracts were washed with brine (20 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe crude product was purified by chromatography on silica gel (5 g)
  9. washeluting with hexane ether (2:1)

Sources & evidence

ORD record
ord-e8ec546d476d4867b475b236b5137719
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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