4-Methylmorpholine → 2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-5-cyano-1-(4-benzyloxyphenylcarbamoylmethyl)-benzimidazole

HRID 412546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412546
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:34][C:35]3[N:39]([CH2:40][C:41](O)=[O:42])[C:38]4[CH:44]=[CH:45][C:46]([C:48]#[N:49])=[CH:47][C:37]=4[N:36]=3)[C:22](=[O:33])[C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.Cl.[CH2:62]([O:69][C:70]1[CH:76]=[CH:75][C:73]([NH2:74])=[CH:72][CH:71]=1)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]([CH2:34][C:35]3[N:39]([CH2:40][C:41](=[O:42])[NH:74][C:73]4[CH:72]=[CH:71][C:70]([O:69][CH2:62][C:63]5[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=5)=[CH:76][CH:75]=4)[C:38]4[CH:44]=[CH:45][C:46]([C:48]#[N:49])=[CH:47][C:37]=4[N:36]=3)[C:22](=[O:33])[C:23]3[CH:24]=[CH:25][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:28]=3)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 5

HCID 79724-MethylmorpholineHCID 27238314-Benzyloxyaniline hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 185364772-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonylbenzoyl)aminomethyl]-5-cyanobenzimidazole-1-acetic acid

Produkt 1

HCID 185365182-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-5-cyano-1-(4-benzyloxyphenylcarbamoylmethyl)-benzimidazoleAusbeute 75,3 %

Versuchsvorschrift

2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonylbenzoyl)aminomethyl]-5-cyanobenzimidazole-1-acetic acid (632 mg), 1-hydroxybenzotriazole hydrate (128 mg), 4-benzyloxyaniline hydrochloride (223 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (182 mg) and N-methylmorpholine (0.104 ml) were treated in the same manner as in Example 17, Step 10. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:7-2:8) to give the title compound (605 mg).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:7-2:8)

Quellen und Nachweise

ORD-Eintrag
ord-15560a0139cd4e73b31dafef9908e927
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562828B1

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