Dimethylformamide → 4-(4-Trifluoromethylpyrid-3-ylcarbonylamino)-2-phenylbenzoic acid 2-trimethylsilylethyl ester

HRID 2121224Notes

Reaction equation

HRID 2121224 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([C:9]([OH:11])=O)=[CH:7][N:6]=[CH:5][CH:4]=1.[CH3:14][Si:15]([CH3:43])([CH3:42])[CH2:16][CH2:17][O:18][C:19](=[O:41])[C@H:20](CCSC)NC(=O)C1C=CC(N)=CC=1C1C=CC=CC=1.ON1[C:50](=O)[C:49]2[CH:52]=[CH:53][CH:54]=[CH:55][C:48]=2N=N1.CN(C)[CH2:58][CH2:59][CH2:60][N:61]=C=NCC.[CH3:67]N(C=O)C>C(OCC)(=O)C>[CH3:43][Si:15]([CH3:14])([CH3:42])[CH2:16][CH2:17][O:18][C:19](=[O:41])[C:20]1[CH:58]=[CH:59][C:60]([NH:61][C:9]([C:8]2[CH:7]=[N:6][CH:5]=[CH:4][C:3]=2[C:2]([F:1])([F:13])[F:12])=[O:11])=[CH:67][C:50]=1[C:49]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:48]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-HCID 67550574(4-Amino-2-phenylbenzoyl)methionine 2-trimethylsilylethyl ester

Product 1

HCID 675506874-(4-Trifluoromethylpyrid-3-ylcarbonylamino)-2-phenylbenzoic acid 2-trimethylsilylethyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-trifluoromethylnicotinic acid (472 mg, 2.46 mmol), the product of Example 283B (771 mg, 2.46 mmol), 3-hydroxy1,2,3-benzotriazin-4(3H)-one (481 mg, 2.95 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (566 mg, 2.95 mmol) in DMF (8 mL) was stirred room temperature for 15 hours. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (30% ethyl acetate-hexane) to give the title compound (1.04 g, 87%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (30% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c6cdba06c24b4b199e583239ce868c01
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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