Dimethylamine → HCID 67498000, compound

HRID 74166Notes

Reaction equation

HRID 74166 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:26]=[CH:25][C:13]2[N:14]([CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:15]([CH2:17]O)=[N:16][C:12]=2[CH:11]=1.C(Cl)(=O)C(Cl)=O.[I-].[Na+].[CH3:35][NH:36][CH3:37]>CN(C)C=O.C(Cl)(Cl)Cl.O1CCCC1.ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:26]=[CH:25][C:13]2[N:14]([CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:15]([CH2:17][N:36]([CH3:37])[CH3:35])=[N:16][C:12]=2[CH:11]=1

Participants

9

Reactant 4

HCID 674DimethylamineHCID 5238Sodium IodideHCID 65578Oxalyl chlorideHCID 49821381HCID 49821381, compound

Product 1

HCID 67498000HCID 67498000, compoundYield 38%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

An eggplant flask was charged with 5-(benzothiazol-2-yl)-2-hydroxymethyl-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 8) (0.431 g, 1.179 mmol), oxalyl chloride (0.178 g, 1.40 mmol), and anhydrous dichloromethane (22 mL), and after the addition of anhydrous N,N-dimethylformamide (5 drops) at room temperature, this was refluxed for 3.5 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. To the yellow residue was added anhydrous tetrahydrofuran (1 mL) and anhydrous sodium iodide (0.267 g, 1.78 mmol), followed by a tetrahydrofuran solution of dimethylamine (2.0 M, 5 mL), and this was refluxed for 16 hours. After being allowed to cool to room temperature, the solvent was distilled off under reduced pressure. An adsorbed silica gel powder was prepared from the yellow residue (0.8 g) using chloroform (approx. 30 mL) and silica gel (3.2 g), and this was purified by silica gel column chromatography (silica gel: 32 g, MeOH/CHCl3=1/20) to yield the title compound (0.176 g, 38.0% yield) as a pale yellow powder.

Workup

  1. temperaturethis was refluxed for 3.5 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. temperaturethis was refluxed for 16 hours
  4. temperatureto cool to room temperature
  5. distillationthe solvent was distilled off under reduced pressure
  6. customAn adsorbed silica gel powder was prepared from the yellow residue (0.8 g)
  7. customthis was purified by silica gel column chromatography (silica gel: 32 g, MeOH/CHCl3=1/20)

Sources & evidence

ORD record
ord-bb6944fa21ee4789b9ff128fc1850e00
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

Loading…