Dimethyl Sulfoxide → HCID 59421743, compound

HRID 499921Notes

Reaction equation

HRID 499921 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH2:7][O:8][C:9]([C:11]1[N:12]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[CH:13]=[C:14]([NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[CH3:27])=[O:18])[N:15]=1)=[O:10])=[O:4].[I-].[Na+].[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.CS(C)=O>COCCOC>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:17]([NH:16][C:14]2[N:15]=[C:11]([C:9]([O:8][CH2:7][CH2:6][O:5][C:3](=[O:4])[CH2:2][N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)=[O:10])[N:12]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)[CH:13]=2)=[O:18])=[C:21]([CH3:27])[CH:22]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 5238Sodium IodideHCID 8083MorpholineHCID 59421785HCID 59421785, compound

Product 1

HCID 59421743HCID 59421743, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

61.8 mg (0.1 mmol) of 2-[(2-bromoacetyl)oxy]ethyl 4-({[(4-chloro-2-methylphenyl)amino]carbonyl}amino)-1-[4-(trifluoromethyl)benzyl]-1H-imidazole-2-carboxylate (Example 24A) are dissolved in 0.4 ml of 1,2-dimethoxyethane under argon, and 15 mg (0.1 mmol) of sodium iodide and 43.6 mg (0.5 mmol) of morpholine are added. The reaction mixture is heated under reflux for 2 h and then mixed with 0.3 ml of DMSO, filtered and purified by preparative HPLC (Method 9).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 2 h
  3. filtrationfiltered
  4. custompurified by preparative HPLC (Method 9)

Sources & evidence

ORD record
ord-ccb6a04e5eb24083ba42fcaecfc7089a
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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