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

HRID 1271438Notes

Reaction equation

HRID 1271438 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]3[N:20]=[C:21]([CH:24]=[CH:25][C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)[O:22][CH:23]=3)=[O:18])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[OH-].[K+].I[CH3:39]>CC(C)=O>[CH3:39][N:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)=[CH:11][CH:12]=1)[C:17]([C:19]1[N:20]=[C:21]([CH:24]=[CH:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=2)[O:22][CH:23]=1)=[O:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 727876562-[2-(4-Trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-amide

Product 1

HCID 694876312-[2-(4-Trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid methyl-[4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-[2-(4-Trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-amide (40 mg, 0.083 mmol) is dissolved in acetone (0.6 ml), treated with KOH (17 mg, 0.3 mmol) and iodomethane (17.7 mg, 0.12 mmol) and heated to reflux for 5 min. After cooling the mixture is concentrated, taken up in water (10 ml) and extracted with dichloromethane (2×10 ml). The organic layers are dried over sodium sulfate, concentrated in vacuo and purified by flash column chromatography (ethyl acetate/heptane 9:1) yielding 2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid methyl-[4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-amide 12 as a colorless solid. Yield 30 mg (73%); m.p. 127–129° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 min
  3. temperatureAfter cooling the mixture
  4. concentrationis concentrated
  5. extractionextracted with dichloromethane (2×10 ml)
  6. dry with materialThe organic layers are dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by flash column chromatography (ethyl acetate/heptane 9:1)

Sources & evidence

ORD record
ord-26fae3a69eb44c76b7697f9c64cff6a6
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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