Pyridine → HCID 22141217, compound

HRID 1826336Notes

Reaction equation

HRID 1826336 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].N1C=CC=CC=1.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:28]=1>ClCCl>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([NH:20][S:33]([C:29]3[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=3)(=[O:35])=[O:34])[CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 221413223-(3-Hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine

Product 1

HCID 22141217HCID 22141217, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine (Preparation 12, 220 mg, 0.809 mmol) in dichloromethane (5 ml) at room temperature was added pyridine (0.196 ml, 2.42 mmol) then dropwise over 5 minutes 3-pyridinesulfonylchloride (198 mg, 1.21 mmol). The mixture was stirred for 48 hours, concentrated in vacuo and the residue was purified by silica (10 g) column chromatography eluting with ethyl acetate then 90:10:1 ethyl acetate:methanol:ammonia solution (0.880). Product-containing fractions were combined and concentrated in vacuo to give the title compound as a pale orange oil (200 mg, 60%).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by silica (10 g) column chromatography
  3. washeluting with ethyl acetate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-769a57f367b94a0b991aac66600cd29d
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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