Triethylamine → 2-[2-(4-Trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-amide

HRID 1271437Notes

Reaction equation

HRID 1271437 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[O:12][CH:13]=[C:14]([C:16]([OH:18])=O)[N:15]=2)=[CH:5][CH:4]=1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[N:39]1([CH2:44][CH2:45][CH2:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([NH2:54])=[CH:50][CH:49]=2)[CH:43]=[CH:42][N:41]=[N:40]1>ClCCl.C(OCC)(=O)C>[N:39]1([CH2:44][CH2:45][CH2:46][CH2:47][C:48]2[CH:49]=[CH:50][C:51]([NH:54][C:16]([C:14]3[N:15]=[C:11]([CH:10]=[CH:9][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:20])[F:19])=[CH:8][CH:7]=4)[O:12][CH:13]=3)=[O:18])=[CH:52][CH:53]=2)[CH:43]=[CH:42][N:41]=[N:40]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 184535324-(4-[1,2,3]Triazol-1-yl-butyl)-phenylamineHCID 694874342-{2-[4-(Trifluoromethyl)phenyl]ethenyl}-1,3-oxazole-4-carboxylic acid

Product 1

HCID 727876562-[2-(4-Trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[2-(4-Trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid (100 mg, 0.35 mmol), N-ethyl-N′-(3-dimethyl-aminopropyl)carbodiimide hydrochloride (101 mg, 0.53 mmol), 1-Hydroxybenzotriazole hydrate (73 mg, 0.53 mmol) and triethylamine (71 mg, 0.71 mmol) are suspended in dichloromethane (5 ml). After stirring at room temperature for 15 min 4-(4-[1,2,3]Triazol-1-yl-butyl)-phenylamine (84 mg, 0.39 mmol) is added and stirring is continued for 20 h. Ethyl acetate (10 ml) is added and the mixture washed with aq. HCl (1N, 10 ml), sat. NaHCO3, (10 ml), dried over sodium sulfate and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate/heptane 9:1) yielding 2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-amide 11 as a colorless solid. Yield 109 mg (64%); m.p. 183–185° C.

Workup

  1. additionis added
  2. washthe mixture washed with aq. HCl (1N, 10 ml), sat. NaHCO3, (10 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash column chromatography (ethyl acetate/heptane 9:1)

Sources & evidence

ORD record
ord-cceee2bdfecf4a319ff162115d84d0bc
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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