Formic Acid → N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

HRID 536550ノート

反応式

HRID 536550 の反応式
[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([N:17]2[C:21](=[O:22])[N:20](CC=C)[C:19]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[N:18]2)(=[O:16])=[O:15])=[C:10]([O:33][CH3:34])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)=O.C(N(CC)CC)C>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([N:17]2[C:21](=[O:22])[NH:20][C:19]([C:26]3[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=3)=[N:18]2)(=[O:16])=[O:15])=[C:10]([O:33][CH3:34])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 46238665N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-prop-2-en-1-yl-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

生成物 1

HCID 135927695N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

An amount of 194 mg (0.384 mmol) of N-tert-butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-prop-2-en-1-yl-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide from Example 1 was dissolved under argon in 2 ml of degassed dioxane and admixed with 18 mg (0.015 mmol) of tetrakis(triphenylphosphine)palladium(0), 29 μl (0.77 mmol) of formic acid and 134 μl (0.96 mmol) of triethylamine. The mixture was stirred under reflux for 2 h. The dioxane was concentrated on a rotary evaporator and the residue in the flask was taken up in methanol. It was filtered over kieselguhr, the solid product was washed with methanol and the solvent was removed on a rotary evaporator. Ethyl acetate was added to the residue in the flask. Washing with water was carried out twice. The organic phase was dried over sodium sulphate and freed from the solvent on a rotary evaporator. Purification of the residue by flash chromatography on silica gel (solvent gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate 100%) gave 152 mg (85% of theory) of the target compound.

後処理

  1. temperatureunder reflux for 2 h
  2. concentrationThe dioxane was concentrated on a rotary evaporator
  3. filtrationIt was filtered over kieselguhr
  4. washthe solid product was washed with methanol
  5. customthe solvent was removed on a rotary evaporator
  6. additionEthyl acetate was added to the residue in the flask
  7. washWashing with water
  8. dry with materialThe organic phase was dried over sodium sulphate
  9. customfreed from the solvent on a rotary evaporator
  10. customPurification of the residue by flash chromatography on silica gel (solvent gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate 100%)
  11. customgave 152 mg (85% of theory) of the target compound

出典と根拠

ORDレコード
ord-9bab8e288f014e158a7ff9389e47f2d2
出典データセット
uspto-grants-2014_10
特許番号
US08859601B2

反応ノート

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