Triethylamine → tert-butyl 4-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate

HRID 16580

Reaktionsgleichung

Reaktionsgleichung von HRID 16580
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])([CH3:3])[CH3:2].CCN(CC)CC.[NH2:21][CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH2:25][CH2:24]1.[C:43]([O-])(O)=[O:44].[Na+]>C(Cl)Cl>[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:43]([NH:21][CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH2:25][CH2:24]2)=[O:44])[C:5]1=[O:13])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 16535801-(Propan-2-yl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 67232551tert-Butyl4-{[4-(aminomethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate

Produkt 1

HCID 68584353tert-butyl 4-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of p-nitrophenylchloroformate (4.14 g, 0.0205 mol), 1-isopropyl-1,3-dihydro-2H-benzimidazol-2-one (3.62 g, 0.0205 mol, J. Med. Chem. 1999, 42, 2870-2880) and Et3N (7.81 mL, 0.0560 mol) in CH2Cl2 (100 mL) was stirred at room temperature for 4 h. Then, tert-butyl 4-{[4-(aminomethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate (5.72 g, 0.0187 mol, step 5) was added, and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with sat. NaHCO3 aq. (300 mL), extracted with CH2Cl2 (300 mL) for three times. The combined extract was dried over Na2SO4 and concentrated. The residue was chromatographed on a column of NH-silica gel eluting with hexane/ethyl acetate (1:1) to give 9.83 g (100%) of the title compound as a yellow syrup.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 24 h
  2. extractionextracted with CH2Cl2 (300 mL) for three times
  3. extractionThe combined extract
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a column of NH-silica gel eluting with hexane/ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-b49458cd1d814d27a3393d2ce0833f76
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737163B2

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