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

HRID 720870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720870
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([OH:16])=O)[N:11]=[C:10]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([NH:25][C:26]([NH:28][N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[O:27])[C:22]=4[C:23](=[O:24])[C:9]=23)=[CH:4][CH:3]=1.[NH2:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][NH:47][C:48]([CH2:50][CH2:51][C@H:52]([NH:60][C:61]([C:63]1[CH:68]=[CH:67][C:66]([N:69](C(OCC2C=CC=CC=2)=O)[CH3:70])=[CH:65][CH:64]=1)=[O:62])[C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[O:49].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>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([NH:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][NH:47][C:48]([CH2:50][CH2:51][C@H:52]([NH:60][C:61]([C:63]3[CH:64]=[CH:65][C:66]([NH:69][CH3:70])=[CH:67][CH:68]=3)=[O:62])[C:53]([O:55][C:56]([CH3:57])([CH3:58])[CH3:59])=[O:54])=[O:49])=[O:16])[N:11]=[C:10]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([NH:25][C:26](=[O:27])[NH:28][N:29]5[CH2:30][CH2:31][O:32][CH2:33][CH2:34]5)[C:22]=4[C:23](=[O:24])[C:9]=23)=[CH:4][CH:3]=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 1357740212-{3-(4-Hydroxyphenyl)-5-[(morpholin-4-ylamino)carbonylamino]-4-oxoindeno[3,2-c]pyrazol-2-yl}acetic acid

Produkt 1

HCID 136397846Tert-butyl (2S)-4-{N-[2-(2-{2-[2-(2-{3-(4-hydroxyphenyl)-5-[(N-morpholin-4-ylcarbamoyl)amino]-4-oxoindeno[3,2-c]pyrazol-2-yl}acetylamino)ethoxy]ethoxy}ethoxy) ethyl]carbamoyl}-2-{[4-(methylamino)phenyl]carbonylamino}butanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Compound 38 (0.52 g, 1.1 mmol) and compound 12 (0.55 g, 1.1 mmol) were dissolved in 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 overnight, diluted with EtOAc and the organic phase washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated to an oil. This oil was purified by flash silica chromatography (1 to 2 to 3 to 4 to 5% MeOH/CH2Cl2) to give a yellow foam (0.45 g, 0.47 mmol, 43%, compound 39).

Aufarbeitung

  1. washthe organic phase washed with saturated NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil
  5. customThis oil was purified by flash silica chromatography (1 to 2 to 3 to 4 to 5% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-33fd9d67442c41eb91158edb629cc688
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135550B2

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