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Diisopropylethylamine → HCID 178495706, Verbindung

HRID 1413002
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1413002
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][N:7](C(OC(C)(C)C)=O)[C@H:6]([C:16]2[NH:17][C:18]([C:21]3[CH:26]=[C:25]4[CH2:27][O:28][C:29]5[CH:47]=[C:46]6[C:32]([CH:33]=[CH:34][C:35]7[N:39]=[C:38]([C@@H:40]8[CH2:44][CH2:43][C@H:42]([CH3:45])[NH:41]8)[NH:37][C:36]=76)=[CH:31][C:30]=5[C:24]4=[CH:23][CH:22]=3)=[CH:19][N:20]=2)[CH2:5]1.[CH3:48][O:49][C@H:50]([CH3:60])[C@H:51]([NH:55][C:56]([O:58][CH3:59])=[O:57])[C:52](O)=[O:53].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:59][O:58][C:56](=[O:57])[NH:55][C@@H:51]([C@H:50]([O:49][CH3:48])[CH3:60])[C:52]([N:41]1[C@@H:42]([CH3:45])[CH2:43][CH2:44][C@H:40]1[C:38]1[NH:37][C:36]2[C:46]3[C:32]([CH:33]=[CH:34][C:35]=2[N:39]=1)=[CH:31][C:30]1[C:24]2[C:25]([CH2:27][O:28][C:29]=1[CH:47]=3)=[CH:26][C:21]([C:18]1[NH:17][C:16]([C@@H:6]3[CH2:5][C@H:4]([CH2:3][O:2][CH3:1])[CH2:8][NH:7]3)=[N:20][CH:19]=1)=[CH:22][CH:23]=2)=[O:53]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59540170(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acidHCID 178495689HCID 178495689, Verbindung

Produkt 1

HCID 178495706HCID 178495706, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl(2S,4S)-4-(methoxymethyl)-2-(5-{2-[(2S,5S)-5-methylpyrrolidin-2-yl]-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (101 mg, 0.159 mmol), (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid (30 mg, 0.159 mmol), HATU (61 mg, 0.159 mmol) and 2 mL 10% DIPEA in DMF was stirred at room temperature for 1.5 hours. Saturated sodium bicarbonate was added and the product was extracted into dichloromethane, dried over sodium sulphate, filtered and concentrated under reduced pressure. This crude product was treated with 5 mL 1.25N HCl in ethanol at 50° C. for 4 h and then it was concentrated under reduced pressure. Saturated sodium bicarbonate was added and the product was extracted into dichloromethane, dried over sodium sulphate, filtered and concentrated under reduced pressure. (74.6 mg)

Aufarbeitung

  1. extractionthe product was extracted into dichloromethane
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionThis crude product was treated with 5 mL 1.25N HCl in ethanol at 50° C. for 4 h
  6. concentrationit was concentrated under reduced pressure
  7. additionSaturated sodium bicarbonate was added
  8. extractionthe product was extracted into dichloromethane
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-257ae11e8e224a97af72e338b441c329
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08921341B2

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