Dimethyl Sulfoxide → HCID 23057953, compound

HRID 346501Notes

Reaction equation

HRID 346501 reaction equation
[OH-].[K+].CS(C)=O.[N:7]1([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([C:23]4[NH:24][C:25]5[C:30]([CH:31]=4)=[CH:29][CH:28]=[CH:27][CH:26]=5)=[N:21][N:22]=3)[N:19]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH3:32]I>O>[N:7]1([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([C:23]4[N:24]([CH3:32])[C:25]5[C:30]([CH:31]=4)=[CH:29][CH:28]=[CH:27][CH:26]=5)=[N:21][N:22]=3)[N:19]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 135736074HCID 135736074, compound

Product 1

HCID 23057953HCID 23057953, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of potassium hydroxide (98 mg) and DMSO (5 ml), 6-azepan-1-yl-3-(1H-indol-2-yl)-1,2,4-triazolo[4,3-b]pyridazine (501 mg) was added, and the mixture was stirred at room temperature for 30 minutes, and then combined with methyl iodide (0.15 ml) and then stirred for further 2 hours at room temperature. The reaction mixture was combined with water, and the resultant solids were collected by filtration, washed with a solvent a mixture of water and methanol, and then purified by silica gel column chromatography (eluent: chloroform: methanol=99:1). The resultant crude crystals were recrystallized from ethanol to obtain 6-azepan-1-yl-3-(1-methylindol-2-yl)-1,2,4-triazolo[4,3-b]pyridazine (40 mg) as colorless crystals.

Workup

  1. additionwas added
  2. stirringstirred for further 2 hours at room temperature
  3. filtrationthe resultant solids were collected by filtration
  4. washwashed with a solvent
  5. additiona mixture of water and methanol
  6. custompurified by silica gel column chromatography (eluent: chloroform: methanol=99:1)
  7. customThe resultant crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-6a6b142783ae4168aa6ee1de95716142
Source dataset
uspto-grants-2007_02
Patent number
US07173033B2

Reaction notes

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