Diisopropylethylamine → Tert-butyl (2S)-2-{[4-(methylamino)phenyl]carbonylamino}-4-(N-{2-[2-(2-{2-[2-(4-{5-[(N-morpholin-4-ylcarbamoyl)amino]-4-oxoindeno[3,2-c]pyrazol-3-yl}phenoxy)acetylamino]ethoxy}ethoxy)ethoxy]ethyl}carbamoyl)butanoate

HRID 720867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720867
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][C:14]([CH2:16][CH2:17][C@H:18]([NH:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([N:35](C(OCC2C=CC=CC=2)=O)[CH3:36])=[CH:31][CH:30]=1)=[O:28])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:15].[N:47]1([NH:53][C:54]([NH:56][C:57]2[C:62]3[C:63](=[O:80])[C:64]4[C:65](=[N:66][NH:67][C:68]=4[C:69]4[CH:79]=[CH:78][C:72]([O:73][CH2:74][C:75](O)=[O:76])=[CH:71][CH:70]=4)[C:61]=3[CH:60]=[CH:59][CH:58]=2)=[O:55])[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:36][NH:35][C:32]1[CH:31]=[CH:30][C:29]([C:27]([NH:26][C@@H:18]([CH2:17][CH2:16][C:14](=[O:15])[NH:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:75](=[O:76])[CH2:74][O:73][C:72]2[CH:71]=[CH:70][C:69]([C:68]3[NH:67][N:66]=[C:65]4[C:61]5[CH:60]=[CH:59][CH:58]=[C:57]([NH:56][C:54](=[O:55])[NH:53][N:47]6[CH2:48][CH2:49][O:50][CH2:51][CH2:52]6)[C:62]=5[C:63](=[O:80])[C:64]=34)=[CH:79][CH:78]=2)[C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])=[O:28])=[CH:34][CH:33]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66910315HCID 66910315, VerbindungHCID 1785259502-(4-(5-[(morpholin-4-ylamino)carbonylamino]-4-oxoindeno[3,2-c]pyrazol-3-yl}phenoxy)acetic Acid

Produkt 1

HCID 178482176Tert-butyl (2S)-2-{[4-(methylamino)phenyl]carbonylamino}-4-(N-{2-[2-(2-{2-[2-(4-{5-[(N-morpholin-4-ylcarbamoyl)amino]-4-oxoindeno[3,2-c]pyrazol-3-yl}phenoxy)acetylamino]ethoxy}ethoxy)ethoxy]ethyl}carbamoyl)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Compound 12 (0.71 g, 1.4 mmol) and compound 25 (0.57 g, 1.2 mmol) were dissolved in 10 ml DMF and HBTU (0.8 g, 2.1 mmol) was added as a solid followed by DIEA (0.52 ml, 3 mmol). The reaction mixture was stirred at room temperature for 3 days, diluted with EtOAc and the organic phase washed with saturated NaHCO3. The aqueous layer was back extracted with EtOAc twice and the combined organic layers dried over MgSO4, filtered and concentrated to an oil. This oil was purified by flash silica chromatography (2 to 5% MeOH/EtOAc) to give an orange oil (0.50 g, 0.52 mmol, 44%, compound 27).

Aufarbeitung

  1. washthe organic phase washed with saturated NaHCO3
  2. extractionThe aqueous layer was back extracted with EtOAc twice
  3. dry with materialthe combined organic layers dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThis oil was purified by flash silica chromatography (2 to 5% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-7783565767084e62bb51a84c3a0aea72
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135550B2

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