N,N-Dimethylglycine → HCID 57665233, compound

HRID 1717401Notes

Reaction equation

HRID 1717401 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)=[C:15]([C:26]([NH:28][CH2:29][CH2:30][OH:31])=[O:27])[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH3:32][N:33]([CH3:38])[CH2:34][C:35](O)=[O:36].CCN=C=NCCCN(C)C.O>N1C=CC=CC=1>[CH3:32][N:33]([CH3:38])[CH2:34][C:35]([O:31][CH2:30][CH2:29][NH:28][C:26]([C:15]1[N:14]=[N:13][N:12]([C:9]2[CH:8]=[CH:7][C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=2)[C:16]=1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)=[O:27])=[O:36]

Participants

6

Reactant 4

HCID 673N,N-DimethylglycineHCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 57665008HCID 57665008, compound

Product 1

HCID 57665233HCID 57665233, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-{4-[(ethylamino)carbonyl]phenyl}-5-[(3-fluorophenoxy)methyl]-N-(2-hydroxyethyl)-1H-1,2,3-triazole-4-carboxamide (500 mg) obtained in Example 498 in pyridine (10 ml) were added dimethylglycine (181 mg) and WSC (336 mg), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column (ethyl acetate/hexane=1/1 to 2/1) and recrystallized from ethyl acetate to give the title compound as a colorless powder (432 mg).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washwashed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by basic silica gel column (ethyl acetate/hexane=1/1 to 2/1)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d584cbf976a54b078a3de29f8b56fb62
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

Loading…