Triethylamine → N-3-biphenylyl-N'-{4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}urea

HRID 1727689

Reaktionsgleichung

Reaktionsgleichung von HRID 1727689
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][CH:15]=[CH:16][C:9]=23)[C:5]([C:17]2[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=2)=[N:4]1)[CH3:2].C(N(CC)CC)C.Cl[C:32](OC1C=CC([N+]([O-])=O)=CC=1)=[O:33].[C:44]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:49]=[CH:48][CH:47]=[C:46]([NH2:50])[CH:45]=1>O1CCCC1.O>[C:44]1([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:49]=[CH:48][CH:47]=[C:46]([NH:50][C:32]([NH:21][C:20]2[CH:22]=[CH:23][C:17]([C:5]3[C:6]([C:8]4[CH:13]=[CH:12][N:11]=[C:10]5[NH:14][CH:15]=[CH:16][C:9]=45)=[CH:7][N:3]([CH2:1][CH3:2])[N:4]=3)=[CH:18][CH:19]=2)=[O:33])[CH:45]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 167173-AminobiphenylHCID 821294-Nitrophenyl chloroformateHCID 689998134-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]aniline

Produkt 1

HCID 58980021N-3-biphenylyl-N'-{4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}ureaAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]aniline (0.23 mmol) in tetrahydrofuran (1 mL) was treated with triethylamine (0.23 mmol) and 4-nitrophenyl chloroformate (0.23 mmol). The reaction stirred for 1 h at room temperature and was then treated with 3-biphenylamine (5 eq). After stirring 18 h at room temperature the reaction was poured into water (1 mL), and extracted with (3×1 mL) ethyl acetate. The combined organic layers were washed with 1N sodium hydroxide (3×1 mL), brine (1×1 mL), dried over sodium sulfate and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC provided the title product as a white powder (45%). ESMS [M+H]+: 499.2

Aufarbeitung

  1. stirringAfter stirring 18 h at room temperature the reaction
  2. extractionextracted with (3×1 mL) ethyl acetate
  3. washThe combined organic layers were washed with 1N sodium hydroxide (3×1 mL), brine (1×1 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by Gilson reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0d8b4f10022d466eaa1b50e8ae33497d
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495102B2

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