Dimethylamine → HCID 24750600, compound

HRID 643703Notes

Reaction equation

HRID 643703 reaction equation
[CH3:1][NH:2][CH3:3].Cl.[CH:5]1([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][C:16]([S:18]([C:21]([CH3:26])([CH3:25])[C:22](Cl)=[O:23])(=[O:20])=[O:19])=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:7][CH2:6]1>ClCCl>[CH:5]1([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][C:16]([S:18]([C:21]([CH3:26])([CH3:25])[C:22]([N:2]([CH3:3])[CH3:1])=[O:23])(=[O:20])=[O:19])=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86630621HCID 86630621, compound

Product 1

HCID 24750600HCID 24750600, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of dimethylamine (2 mol/L tetrahydrofurane solution, 0.950 mL, 1.90 mmol) in dichloromethane (3 mL) was added 2-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropanoyl chloride hydrochloride (Step A, 175 mg, 0.380 mmol) in dichloromethane (2 mL) at room temperature. After stirring at the same temperature for 1.5 h, the mixture was diluted with dichloromethane. The whole was washed with saturated sodium hydrogencarbonate aqueous solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by HPLC (ODS, gradient elution with acetonitrile/0.01% aq. NH3=4:96 to 96:4, by volume; flow rate 40 mL/min) to afford the title compound (75 mg, 47%) as an amorphous.

Workup

  1. washThe whole was washed with saturated sodium hydrogencarbonate aqueous solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by HPLC (ODS, gradient elution with acetonitrile/0.01% aq. NH3=4:96 to 96:4, by volume; flow rate 40 mL/min)

Sources & evidence

ORD record
ord-09b0c9707b4a41048c5228546fbf3c38
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

Loading…