Pyridine → HCID 58300410, compound

HRID 68647Notes

Reaction equation

HRID 68647 reaction equation
[CH2:1]([N:4]([CH2:28][CH2:29][CH3:30])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][NH:20][CH2:21][C:22]3[N:23]([CH3:27])[CH:24]=[CH:25][N:26]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH3:3].N1C=CC=CC=1.Cl.[NH:38]1[CH:42]=[CH:41][N:40]=[C:39]1[S:43](Cl)(=[O:45])=[O:44].[OH-].[Na+]>ClCCl>[CH2:28]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][N:20]([CH2:21][C:22]3[N:23]([CH3:27])[CH:24]=[CH:25][N:26]=3)[S:43]([C:39]3[NH:38][CH:42]=[CH:41][N:40]=3)(=[O:45])=[O:44])[CH:15]=2)[CH2:10]1)[CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 67163530({2-[4-(dipropylamino)butyl]-1,2,3,4-tetrahydro-6-isoquinolinyl}methyl)[(1-methyl-1H-imidazol-2-yl)methyl]amineHCID 713020781H-Imidazole-2-sulfonyl chloride--hydrogen chloride (1/1)

Product 1

HCID 58300410HCID 58300410, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a solution of the compound 23-a (100 mg) and pyridine (59 mL) in dichloromethane (3 mL), the compound 36 (74 mg) was added. The reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture, an aqueous 1N sodium hydroxide solution (15 mL) was added. The aqueous layer was extracted twice with dichloromethane (30 mL). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel chromatography (ethyl acetate:methanol:triethylamine=10:1:0→10:1:0.5) to obtain the title compound (119 mg) having the following physical properties.

Workup

  1. extractionThe aqueous layer was extracted twice with dichloromethane (30 mL)
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol:triethylamine=10:1:0→10:1:0.5)

Sources & evidence

ORD record
ord-6e31bd4520b64b39a4d7c0a6b6d349db
Source dataset
uspto-grants-2014_09
Patent number
US08822459B2

Reaction notes

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