Triethylamine → HCID 86617203, compound

HRID 499910Notes

Reaction equation

HRID 499910 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:8]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[CH:9]=[C:10]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)=[O:14])[N:11]=1)=[O:6].[CH2:38](N(CC)CC)C.BrC[C:47]([Cl:49])=O.[C:50](=[O:53])(O)[O-].[Na+]>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:49][CH2:47][C:50]([O:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:8]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:32][CH:33]=2)[CH:9]=[C:10]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:25])([F:24])[F:26])=[CH:18][C:17]=2[CH3:38])=[O:14])[N:11]=1)=[O:6])=[O:53]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 89602Bromoacetyl chlorideHCID 516892Sodium BicarbonateHCID 59421816HCID 59421816, compound

Product 1

HCID 86617203HCID 86617203, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

850 mg (1.6 mmol) of N-(2-hydroxyethyl)-4-[({[4-(trifluoromethoxy)phenyl]amino}-carbonyl)amino]-1-[4-(trifluoromethyl)benzyl]-1H-imidazole-2-carboxamide (Example 124) are dissolved in 3.2 ml of absolute DMF under argon, and a few crystals of DMAP and 647 mg (892 μl, 6.4 mmol) of triethylamine are added. While cooling in ice, 755 mg (400 μl, 4.8 mmol) of bromoacetyl chloride are added dropwise. The reaction mixture is stirred at RT for 1.5 h and then poured into cold saturated sodium bicarbonate solution and extracted twice with ethyl acetate. The combined extracts are washed once with water and three times with saturated sodium chloride solution, dried with magnesium sulphate and evaporated in vacuo.

Workup

  1. temperatureWhile cooling in ice
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts are washed once with water and three times with saturated sodium chloride solution
  4. dry with materialdried with magnesium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-0b78cd6acd3848c78b1f2d1d8271a8e3
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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