Triethylamine → N-[4-(1-ethyl-4-{2-[4-(4-morpholinylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazol-3-yl)phenyl]-4-thiomorpholinecarboxamide 1,1-dioxide

HRID 28894

Reaktionsgleichung

Reaktionsgleichung von HRID 28894
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][N:24]5[CH2:29][CH2:28][O:27][CH2:26][CH2:25]5)=[CH:19][CH:18]=4)=[CH:16][C:9]=23)[C:5]([C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=2)=[N:4]1)[CH3:2].C(N(CC)CC)C.Cl[C:45](OC(C)=C)=[O:46].[NH:51]1[CH2:56][CH2:55][S:54](=[O:58])(=[O:57])[CH2:53][CH2:52]1>C1COCC1>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH:18]=[CH:19][C:20]([CH2:23][N:24]5[CH2:25][CH2:26][O:27][CH2:28][CH2:29]5)=[CH:21][CH:22]=4)=[CH:16][C:9]=23)[C:5]([C:30]2[CH:31]=[CH:32][C:33]([NH:34][C:45]([N:51]3[CH2:56][CH2:55][S:54](=[O:58])(=[O:57])[CH2:53][CH2:52]3)=[O:46])=[CH:35][CH:36]=2)=[N:4]1)[CH3:2]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 93846Isopropenyl chloroformateHCID 6484228Thiomorpholine 1,1-dioxideHCID 689981684-(1-ethyl-4-{2-[4-(4-morpholinylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazol-3-yl)aniline

Produkt 1

HCID 58980003N-[4-(1-ethyl-4-{2-[4-(4-morpholinylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazol-3-yl)phenyl]-4-thiomorpholinecarboxamide 1,1-dioxideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(1-ethyl-4-{2-[4-(4-morpholinylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazol-3-yl)aniline (0.25 mmol) in anhydrous THF (2 mL) cooled to 5° C., was added triethylamine (4 mmol) and isopropenyl chloroformate (0.5 mmol). The reaction mixture was stirred overnight at room temperature. Thiomorpholine 1,1-dioxide (2.5 mmol) was added and the reaction heated at 50° C. for three days. The crude reaction was purified by reverse phase chromatography to give the title product (30%). ESMS [M+H]+: 640.0.

Aufarbeitung

  1. temperaturethe reaction heated at 50° C. for three days
  2. customThe crude reaction
  3. customwas purified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-abf75457714741d6972343e0af14de02
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419988B2

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