Dimethylamine → HCID 25268815, compound

HRID 1516403Notes

Reaction equation

HRID 1516403 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:34])(=[N:29][C:30](=[O:33])[CH2:31]Cl)=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1.[CH3:35][NH:36][CH3:37]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:22]=[CH:23][C:24]([S:27]([CH3:34])(=[N:29][C:30](=[O:33])[CH2:31][N:36]([CH3:37])[CH3:35])=[O:28])=[CH:25][CH:26]=2)=[O:20])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 25267405HCID 25267405, compound

Product 1

HCID 25268815HCID 25268815, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirring solution of S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-chlorophenyl}carbamoyl)phenyl]-S-methyl-N-chloroacetyl sulfoximide (100 mg, 0.185 mmol, Example 6) in DMF (0.2 mL) was added 50% aqueous dimethylamine solution (164 mg, 0.162 mmol) followed by catalytic amount of KI. The reaction mixture was stirred at 25-30° C. for 12 hr and then diluted with water (5 mL). Filtration and drying afforded 50 mg of titled compound in 49% yield.

Workup

  1. filtrationFiltration
  2. customdrying

Sources & evidence

ORD record
ord-56e602631f454c85897951e2645746fd
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

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