Dimethylformamide → HCID 178483857, compound

HRID 2423252Notes

Reaction equation

HRID 2423252 reaction equation
CNC.C1COCC1.[CH3:9][N:10]([CH:12]=O)[CH3:11].ClC[C:16](=[NH:49])[NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27](=[O:48])[C:28](=[C:39]2[NH:43][C:42]3[CH:44]=[CH:45][CH:46]=[CH:47][C:41]=3[NH:40]2)[C:29]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[CH:32]=2)=[O:30])[CH:22]=1)(=[O:20])=[O:19]>O>[F:37][C:35]1[CH:36]=[C:31]([C:29](=[O:30])[C:28](=[C:39]2[NH:40][C:41]3[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=3[NH:43]2)[C:27]([C:23]2[CH:22]=[C:21]([S:18]([NH:17][C:16](=[NH:49])[CH2:12][N:10]([CH3:9])[CH3:11])(=[O:19])=[O:20])[CH:26]=[CH:25][CH:24]=2)=[O:48])[CH:32]=[C:33]([F:38])[CH:34]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 22320367Dimethylamine tetrahydrofuranHCID 178511098HCID 178511098, compound

Product 1

HCID 178483857HCID 178483857, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 M dimethylamine/THF solution (0.85 mL) was added to a DMF (5 mL) solution of 2-chloro-N-({3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}sulfonyl)ethanimidamide (181 mg), followed by stirring at room temperature for 1 hour. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=50/1), and recrystallized from ethyl acetate/n-hexane to obtain N-({3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}sulfonyl)-2-(dimethylamino)ethanimidamide (76 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform/methanol=50/1)
  5. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-ae1700c904404996afc0e6ea5b50c1df
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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