2,5-Dimethoxytetrahydrofuran → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-(pyrrol-1-yl)-5-fluoro phenyl]piperidin-3-ol

HRID 1392399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392399
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=3[NH2:35])[CH2:24][CH:23]2[OH:36])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].CO[CH:39]1[CH2:43][CH2:42][CH:41](OC)O1>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=3[N:35]3[CH:39]=[CH:43][CH:42]=[CH:41]3)[CH2:24][CH:23]2[OH:36])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11]

Komponenten

3

Edukt 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 693155514-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-amino-5-fluorophenyl)piperidin-3-ol

Produkt 1

HCID 693103044-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-(pyrrol-1-yl)-5-fluoro phenyl]piperidin-3-ol

Versuchsvorschrift

The mixture of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-amino-5-fluorophenyl)piperidin-3-ol (2 g) obtained in Step 1 and 0.96 ml of 2,5-dimethoxytetrahydrofuran was refluxed for 1 hour and concentrated under reduced pressure. The resulting residue was diluted with 70 ml of dichloromethane, washed with a saturated sodium bicarbonate solution and brine. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 1.8 g of the titled compound as white color.

Aufarbeitung

  1. temperaturewas refluxed for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. additionThe resulting residue was diluted with 70 ml of dichloromethane
  4. washwashed with a saturated sodium bicarbonate solution and brine
  5. customThe resulting organic layer was dried
  6. concentrationconcentrated on sodium sulfate
  7. customThe resulting residue was purified with column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bc95437e573341cab8722da7accdf3f2
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342027B2

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