Tetrahydrofuran → [4-(4-Trifluoromethylpyrid-3-ylcarboxyamino)-2-phenylbenzoyl]methionine methyl ester

HRID 2121221Notes

Reaction equation

HRID 2121221 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:8](C(O)=O)=[CH:7][N:6]=[CH:5][CH:4]=1.Cl.[CH3:15][O:16][C:17](=[O:39])[C@H:18]([CH2:35][CH2:36][S:37][CH3:38])[NH:19][C:20](=[O:34])[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.ON1[C:46](=[O:47])C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C1C[O:66]CC1>C(OCC)(=O)C>[CH3:15][O:16][C:17](=[O:39])[C@H:18]([CH2:35][CH2:36][S:37][CH3:38])[NH:19][C:20](=[O:34])[C:21]1[CH:26]=[CH:25][C:24]([N:27]([C:8]2[CH:7]=[N:6][CH:5]=[CH:4][C:3]=2[C:2]([F:1])([F:12])[F:13])[C:46]([OH:47])=[O:66])=[CH:23][C:22]=1[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-HCID 69612387(4-Amino-2-phenylbenzoyl)methionine methyl ester hydrochloride

Product 1

HCID 20622816[4-(4-Trifluoromethylpyrid-3-ylcarboxyamino)-2-phenylbenzoyl]methionine methyl esterYield 57%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-trifluoromethylnicotinic acid (100 mg, 0.523 mmol), (4-amino-2-phenylbenzoyl)methionine methyl ester hydrochloride (206 mg, 0.52 mmol), prepared as in Example 192B, 3-hydroxy1,2,3-benzotriazin-4(3H)-one (120 mg, 0.628 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (125 mg, 0.628 mmol) in THF (5 mL) was stirred 15 hours. The reaction mixture was diluted with ethyl acetate , washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (50% ethyl acetate-hexane) to give the title compound (157 mg, 57%).

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 (50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-02495e4431324cab80a50704c3e290d7
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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