Sodium Chloride → HCID 86686800, compound

HRID 1403159Notes

Reaction equation

HRID 1403159 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:21]1[N:26]=[C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:24]=[C:23]([N:33]2[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[N:35]=[C:34]2[CH:42]([F:44])[F:43])[CH:22]=1.[Cl-].[Na+].S([O-])(O)(=O)=O.[K+]>CN(C)C(=O)C.O1CCCC1.C(OCC)(=O)C>[F:44][CH:42]([F:43])[C:34]1[N:33]([C:23]2[N:24]=[C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[N:26]=[C:21]([NH:17][S:14]([C:11]3[CH:10]=[CH:9][C:8]([CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:13][CH:12]=3)(=[O:15])=[O:16])[CH:22]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:35]=1

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 70519393HCID 70519393, compoundHCID 86686801HCID 86686801, compound

Product 1

HCID 86686800HCID 86686800, compoundYield 16.3%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

4-(Morpholin-4-ylmethyl)benzenesulfonamide (35 mg) was dissolved in N,N-dimethylacetamide (1.25 mL), and 60% sodium hydride (4 mg) was added thereto, followed by stirring at room temperature for 30 minutes. To the reaction mixture was added 1-[6-chloro-2-(morpholin-4-yl)pyrimidin-4-yl]-2-(difluoromethyl)-1H-benzimidazole (50 mg), followed by stirring at 120° C. for 1 hour. The mixture was cooled to room temperature, and then a saturated aqueous sodium chloride solution, ethyl acetate, and tetrahydrofuran were added thereto, followed by neutralization with a 10% aqueous potassium hydrogen sulfate solution, and then the organic layer was extracted. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:80-0:100 and subsequently chloroform:methanol=100:0-80:20) to obtain N-{6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}-4-(morpholin-4-ylmethyl)benzenesulfonamide (13 mg).

Workup

  1. stirringby stirring at 120° C. for 1 hour
  2. temperatureThe mixture was cooled to room temperature
  3. extractionthe organic layer was extracted
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe desiccant was removed by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-be73b91d5ecf401b9094c6fcb3fa67a4
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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