Dimethylformamide → HCID 86677425, Verbindung

HRID 2089708

Reaktionsgleichung

Reaktionsgleichung von HRID 2089708
C(O)(=O)C.[C:5]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C@@H:15]([C:32]2[N:36]=[C:35]([O:37][CH2:38][O:39][C:40]([O:42][CH:43]([CH3:45])[CH3:44])=[O:41])[N:34]([C:46]3[N:51]=[CH:50][CH:49]=[CH:48][N:47]=3)[N:33]=2)[C:16]2[C:17]([F:31])=[C:18]([CH:26]=[C:27]([O:29][CH3:30])[CH:28]=2)[O:19][CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24])=[CH:10][CH:9]=1)(=[NH:7])[NH2:6].CN(C=O)C.[N+]([C:60]1C=C[C:63]([O:66][C:67](=O)[O:68]CCCC)=[CH:62][CH:61]=1)([O-])=O.C(N(CC)CC)C>O.C(OCC)(=O)C>[NH2:7][C:5](=[N:6][C:67]([O:66][CH2:63][CH2:62][CH2:61][CH3:60])=[O:68])[C:8]1[CH:9]=[CH:10][C:11]([NH:14][C@@H:15]([C:32]2[N:36]=[C:35]([O:37][CH2:38][O:39][C:40]([O:42][CH:43]([CH3:45])[CH3:44])=[O:41])[N:34]([C:46]3[N:47]=[CH:48][CH:49]=[CH:50][N:51]=3)[N:33]=2)[C:16]2[C:17]([F:31])=[C:18]([CH:26]=[C:27]([O:29][CH3:30])[CH:28]=2)[O:19][CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24])=[CH:12][CH:13]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 12867351Butyl 4-nitrophenyl carbonateHCID 86677426HCID 86677426, Verbindung

Produkt 1

HCID 86677425HCID 86677425, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of Acetic acid 2-{3-[(R)-(4-carbamimidoylphenylamino)-(5-isopropoxycarbonyloxymethoxy-1-pyrimidin-2-yl-1H-[1,2,4]triazol-3-yl)methyl]-2-fluoro-5-methoxyphenoxy}ethyl ester acetic acid salt (23 mg) obtained in Example 67a and DMF (1 ml), carbonic acid butyl ester 4-nitrophenyl ester [CAS No. 67036-13-9] (10 mg) and triethylamine (50 μl) were added, and the resulting mixture was stirred at room temperature for 63 h. Ethyl acetate and water were added to the mixture, and the organic layer was collected. The organic layer was sequentially washed with water and with saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate) to obtain the captioned compound (16.80 mg).

Aufarbeitung

  1. customthe organic layer was collected
  2. washThe organic layer was sequentially washed with water and with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. customthe filtrate obtained
  6. concentrationwas concentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-35ee7317617b49569393fd7564063ee2
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436009B2

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