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Water → HCID 22141295, compound

HRID 1826344
Notes
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Reaction equation

HRID 1826344 reaction equation
[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6]2.[CH3:24][O:25][CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29].O.ClCCl>N1C=CC=CC=1>[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:28]([CH2:27][CH2:26][O:25][CH3:24])(=[O:30])=[O:29])[CH:20]=[CH:21][CH:22]=2)[CH:3]2[CH:7]1[CH2:6][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 11266768HCID 11266768, compoundHCID 134802212-Methoxyethane-1-sulfonyl chloride

Product 1

HCID 22141295HCID 22141295, compoundYield 1.1%

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Procedure

To a solution of 3-[6-methyl-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl]phenylamine (Preparation 8, 200 mg, 0.65 mmol) in pyridine (2 ml) under nitrogen at 0□ C. was added 2-methoxy-1-ethanesulfonyl chloride (J. Chem. Soc., 1968, 2895; 155 mg, 0.98 mmol), then the mixture was stirred at room temperature for 16 hours. Water (5 ml) and dichloromethane (5 ml) was added, and the mixture stirred for 10 minutes. The organic phase was washed further with water (5 ml), separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica (10 g) column chromatography eluting with ethyl acetate:hexane:ammonia solution (0.880) (20:80:1 then 60:40:1). Product-containing fractions were combined and concentrated in vacuo. The residue was further purified by preparative HPLC (condition 4). Combination and evaporation of appropriate fractions gave the title compound as a pale brown solid (3 mg, 1%).

Workup

  1. stirringthe mixture stirred for 10 minutes
  2. washThe organic phase was washed further with water (5 ml)
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica (10 g) column chromatography
  8. washeluting with ethyl acetate
  9. concentrationconcentrated in vacuo
  10. customThe residue was further purified by preparative HPLC (condition 4)
  11. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-e605d0225d0c4277b47ec664a88a276b
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07049444B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes