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

HRID 271945

Reaktionsgleichung

Reaktionsgleichung von HRID 271945
C(N(CC)CC)C.[NH2:8][C@@H:9]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH2:12][NH:11][C:10]1=[O:23].Cl[C:25](OC1C=CC([N+]([O-])=O)=CC=1)=[O:26].Cl.Cl.[O:39]=[C:40]1[NH:48][C:43]2=[N:44][CH:45]=[CH:46][CH:47]=[C:42]2[N:41]1[CH:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O1CCCC1>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([CH:13]2[CH2:12][NH:11][C:10](=[O:23])[C@H:9]([NH:8][C:25]([N:52]3[CH2:53][CH2:54][CH:49]([N:41]4[C:42]5[C:43](=[N:44][CH:45]=[CH:46][CH:47]=5)[NH:48][C:40]4=[O:39])[CH2:50][CH2:51]3)=[O:26])[CH2:15][CH2:14]2)=[CH:17][CH:18]=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 60037861(3R)-3-Amino-6-(4-hydroxyphenyl)azepan-2-one

Produkt 1

HCID 23656587N-[(3R)-6-(4-Hydroxyphenyl)-2-oxoazepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamideAusbeute 33,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (0.009 mL, 0.091 mmol) was added to a solution of (3R)-3-amino-6-(4-hydroxyphenyl)azepan-2-one (10 mg, 0.045 mmol) and 4-nitrophenyl chloroformate (18 mg, 0.091 mmol) in N,N-dimethylformamide (0.2 mL) and tetrahydrofuran (0.2 mL) at 0° C. After 1 h, 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride (26 mg, 0.091 mmol) and diisopropylethylamine (0.032 mL, 0.182 mmol) were added and the mixture was allowed to warm to ambient temperature. After 18 h, the mixture was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) to give the title compound (7 mg). MS 465.2243 (M+1).

Aufarbeitung

  1. waitAfter 18 h
  2. customthe mixture was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-42f5e957e38c41d8abc4f3041840b200
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452903B2

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