Methanesulfonyl chloride → HCID 22141350, compound

HRID 1826337Notes

Reaction equation

HRID 1826337 reaction equation
[CH2:1]([C:3]1([C:15]2[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=2)[CH:8]2[CH:4]1[CH2:5][N:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7]2)[CH3:2].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH2:1]([C:3]1([C:15]2[CH:16]=[C:17]([NH:21][S:23]([CH3:22])(=[O:25])=[O:24])[CH:18]=[CH:19][CH:20]=2)[CH:8]2[CH:4]1[CH2:5][N:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7]2)[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22141144HCID 22141144, compound

Product 1

HCID 22141350HCID 22141350, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-(6-ethyl-3-hexyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine (Preparation 20, 500 mg, 1.56 mmol) in pyridine (5 ml) at 0° C. under nitrogen was added dropwise over 5 minutes methanesulfonylchloride (0.20 ml, 0.30 g, 2.6 mmol). The mixture was allowed to warm to room temperature and was stirred for 18 hours. The mixture was concentrated in vacuo and the residue was purified by silica (25 g) column chromatography eluting with 50:50:1 ethyl acetate:hexane:ammonia solution (0.880). Product-containing fractions were combined and concentrated in vacuo to give the title compound as a pale yellow oil (180 mg, 33%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica (25 g) column chromatography
  3. washeluting with 50:50:1 ethyl acetate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae47db3f23874ce4b6e07f4f306882f3
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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