4-Oxobutanoic acid → HCID 178522093, Verbindung

HRID 491798

Reaktionsgleichung

Reaktionsgleichung von HRID 491798
Cl.Cl.[NH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([NH:12][C:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][C:14]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)=[O:23])=[O:11])[CH2:6][CH2:5]1.[CH2:32]([CH:37]=O)[CH2:33][C:34](O)=[O:35].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C=O.C(N(CC)CC)C>[O:35]=[C:34]1[CH2:33][CH2:32][CH2:37][N:3]1[C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([NH:12][C:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][C:14]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)=[O:23])=[O:11])[CH2:6][CH2:5]1

Komponenten

9

Edukt 5

HCID 11124-Oxobutanoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 178478721HCID 178478721, Verbindung

Produkt 1

HCID 178522093HCID 178522093, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Trans-3-(4-aminocyclohexylcarbonylamino)-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide dihydrochloride (150 mg) obtained in Example 219 is suspended in dichloromethane (5 ml), and thereto is added triethylamine (129 μl) under ice-cooling, and the mixture is stirred for several minutes. Then, 15% aqueous succinic semialdehyde solution (290 μl) and sodium triacetoxy borohydride (131 mg) are successively added thereto, and under ice-cooling, the mixture is stirred for 0.5 hour. Then, 1-hydroxybenzotriazole (63 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (118 mg) and N,N-dimethylformamide (3 ml) are successively added thereto, and the mixture is stirred at room temperature for 15 hours. The reaction solution is concentrated under reduced pressure, and thereto is poured chloroform. The mixture is washed successively with a saturated aqueous sodium hydrogen carbonate solution, water, and a saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, then ethyl acetate), and the resulting residue is suspended in n-hexane, and collected by filtration to give the title compound (29 mg).

Aufarbeitung

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. stirringthe mixture is stirred for 0.5 hour
  4. stirringthe mixture is stirred at room temperature for 15 hours
  5. concentrationThe reaction solution is concentrated under reduced pressure
  6. additionis poured chloroform
  7. washThe mixture is washed successively with a saturated aqueous sodium hydrogen carbonate solution, water
  8. dry with materiala saturated brine, dried over sodium sulfate
  9. customthe solvent is evaporated under reduced pressure
  10. customThe resulting residue is purified by NH-silica gel column chromatography (eluent
  11. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-5ad8afeebb6c42709fa960d21496a0c1
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531537B2

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