Dimethylformamide → HCID 136334027, Verbindung

HRID 2089652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2089652
C(O)(=O)C.[F:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][C:9]([O:16][CH3:17])=[CH:8][C:7]=1[C@@H:18]([NH:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH2:38])=[NH:37])=[CH:34][CH:33]=1)[C:19]1[NH:23][C:22](=[O:24])[N:21]([C:25]2[N:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[N:20]=1.CN(C=O)C.[N+](C1C=CC([O:55][C:56](=O)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)=CC=1)([O-])=O.C(N(CC)CC)C>C(O)(=O)C>[NH2:37][C:36](=[N:38][C:56](=[O:55])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:35]1[CH:34]=[CH:33][C:32]([NH:31][C@H:18]([C:7]2[CH:8]=[C:9]([O:16][CH3:17])[CH:10]=[C:11]([O:12][CH2:13][CH2:14][OH:15])[C:6]=2[F:5])[C:19]2[NH:23][C:22](=[O:24])[N:21]([C:25]3[N:26]=[CH:27][CH:28]=[CH:29][N:30]=3)[N:20]=2)=[CH:40][CH:39]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 70396Benzoic acid, 4-nitrophenyl esterHCID 1363340284-{[(R)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetic acid salt

Produkt 1

HCID 136334027HCID 136334027, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a mixture of 4-{[(R)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetic acid salt [CAS No. 951803-91-1] (5.6 g) and DMF (200 mL), benzoic acid 4-nitrophenyl ester (2.89 g) and triethylamine (4.7 mL) were added, and the resulting mixture was stirred overnight at room temperature. Acetic acid (6.5 mL) was added to the reaction solution, and then the solvent was evaporated under reduced pressure. The residue obtained was crudely purified by reverse phase silica gel column chromatography (mixed solvent of acetonitrile-water, containing 0.1% of acetic acid), and the crudely purified product obtained was purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate) to obtain the captioned compound (4.48 g).

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue obtained
  3. customwas crudely purified by reverse phase silica gel column chromatography (mixed solvent of acetonitrile-water, containing 0.1% of acetic acid)
  4. customthe crudely purified product obtained
  5. customwas purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-56be890cca4f41b588f99ce39795b565
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436009B2

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