Triethylamine → N-[(2S,6R)-4-(Cyclopropylmethyl)-5-oxo-2-phenyl-1,4-oxazepan-6-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide

HRID 20156

Reaktionsgleichung

Reaktionsgleichung von HRID 20156
C(N(CC)CC)C.[NH2:8][C@@H:9]1[CH2:15][O:14][C@@H:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][N:11]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:10]1=[O:26].Cl[C:28](OC1C=CC([N+]([O-])=O)=CC=1)=[O:29].C(N(C(C)C)CC)(C)C.Cl.Cl.[O:51]=[C:52]1[NH:60][C:55]2=[N:56][CH:57]=[CH:58][CH:59]=[C:54]2[N:53]1[CH:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1>O1CCCC1.ClCCl>[CH:23]1([CH2:22][N:11]2[C:10](=[O:26])[C@H:9]([NH:8][C:28]([N:64]3[CH2:65][CH2:66][CH:61]([N:53]4[C:54]5[C:55](=[N:56][CH:57]=[CH:58][CH:59]=5)[NH:60][C:52]4=[O:51])[CH2:62][CH2:63]3)=[O:29])[CH2:15][O:14][C@@H:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12]2)[CH2:25][CH2:24]1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 60037869(2S,6R)-6-amino-4-(cyclopropylmethyl)-2-phenyl-1,4-oxazepan-5-one

Produkt 1

HCID 11283500N-[(2S,6R)-4-(Cyclopropylmethyl)-5-oxo-2-phenyl-1,4-oxazepan-6-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamideAusbeute 85,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (0.015 mL, 0.109 mmol) was added to a solution of (2S,6R)-6-amino-4-(cyclopropylmethyl)-2-phenyl-1,4-oxazepan-5-one (27 mg, 0.104 mmol) and 4-nitrophenyl chloroformate (22 mg, 0.109 mmol) in tetrahydrofuran (2 mL) at 0° C. After 0.5 h, diisopropylethylamine (0.072 mL, 0.415 mmol), 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride (36 mg, 0.124 mmol), and dichloromethane (2.5 mL) were added and the mixture warmed to ambient temperature. After 18 h, the mixture was concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (45 mg). MS 505.2559 (M+1).

Aufarbeitung

  1. waitAfter 18 h
  2. concentrationthe mixture was concentrated
  3. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-7f4610bd0f7043ccb422dfb89a9be381
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745427B2

Verknüpfte Notizen

Wird geladen…