Potassium Carbonate → HCID 178459239, compound

HRID 237338Notes

Reaction equation

HRID 237338 reaction equation
Cl.[Cl:2][C:3]1[CH:26]=[CH:25][C:6]2[N:7]3[C:11]([CH2:12][NH:13][CH2:14][C:5]=2[CH:4]=1)=[N:10][N:9]=[C:8]3[C@H:15]1[CH2:20][CH2:19][C@H:18]([O:21][CH:22]([CH3:24])[CH3:23])[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].Br.Br[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1>C(#N)C>[Cl:2][C:3]1[CH:26]=[CH:25][C:6]2[N:7]3[C:11](=[N:10][N:9]=[C:8]3[C@H:15]3[CH2:16][CH2:17][C@H:18]([O:21][CH:22]([CH3:24])[CH3:23])[CH2:19][CH2:20]3)[CH2:12][N:13]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[CH2:14][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 178459238HCID 178459238, compound

Product 1

HCID 178459239HCID 178459239, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of trans-8-chloro-1-(4-isopropoxy-cyclohexyl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene hydrochloride (0.070 g, 0.18 mmol) and potassium carbonate (0.073 ml, 0.53 mmol) in acetonitrile (1 ml) was added 2-(bromomethyl)pyridine hydrobromide (0.048 g, 0.18 mmol) at room temperature. Stirring for 20 h at 50° C. was followed by partitioning between 1 M aqueous sodium hydroxide solution (30 ml) and dichloromethane (30 ml). The layers were separated. The aqueous layer was extracted with two 30-ml portions of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash-chromatography with n-heptane/2-propanol as eluent gave the title compound (0.046 g, 58%) as yellow oil. MS m/e: 452 (M+H+).

Workup

  1. customby partitioning between 1 M aqueous sodium hydroxide solution (30 ml) and dichloromethane (30 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with two 30-ml portions of dichloromethane
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash-chromatography with n-heptane/2-propanol as eluent

Sources & evidence

ORD record
ord-b04e4353b0f844b1ad91325efeb401e0
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

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