Water → HCID 22141289, compound

HRID 1826372Notes

Reaction equation

HRID 1826372 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-397c31532c6c48109258c1aaf738a00d
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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