Pyridine → HCID 22141170, compound

HRID 1826332Notes

Reaction equation

HRID 1826332 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH:14]3[CH:12]([C:13]3([C:17]3[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=3)[CH3:16])[CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31]>ClCCl>[CH:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH:14]3[CH:12]([C:13]3([C:17]3[CH:18]=[C:19]([NH:23][S:32]([CH2:30][CH3:31])(=[O:34])=[O:33])[CH:20]=[CH:21][CH:22]=3)[CH3:16])[CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chloride2×HCID 22141223HCID 22141223, compound

Product 1

HCID 22141170HCID 22141170, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-(3-cyclohexylpropyl)-6-methyl-3-azabicyclo[3.1.0]hex-6-yl]phenylamine (Preparation 10, 25 mg, 0.08 mmol) in dichloromethane (2 ml) at 0° C. under nitrogen was added pyridine (20 μl, 0.24 mmol) then dropwise over 5 minutes ethanesulfonylchloride (25 μl, 34 mg, 0.26 mmol). The mixture was allowed to warm to room temperature and was stirred for 1.5 h. Further ethanesulfonylchloride (25 μl, 34 mg, 0.26 mmol) was added and the mixture was stirred for 2 hours. The mixture was concentrated in vacuo and the residue was purified by silica (5 g) column chromatography eluting with 80:20:1 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 (21 mg, 65%).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by silica (5 g) column chromatography
  4. washeluting with 80:20:1 ethyl acetate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9975a402fe1a4e4e8c89178214a6d4eb
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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