Triethylamine → (R)-Quinuclidin-3-yl ((S)-(3-((3-((4,4-diethoxybutyl)carbamoyl)-1-methyl-1H-pyrazol-5-yl)methoxy)phenyl)(phenyl)methyl)carbamate

HRID 877329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877329
[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C@H:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:16][C:17]([O:19][C@@H:20]3[CH:25]4[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]4)[CH2:21]3)=[O:18])[CH:10]=2)=[CH:5][C:4]([C:34](O)=[O:35])=[N:3]1.C(N(CC)CC)C.[CH2:44]([O:46][CH:47]([O:52][CH2:53][CH3:54])[CH2:48][CH2:49][CH2:50][NH2:51])[CH3:45].CCN=C=NCCCN(C)C.OC1C=CC=C[N+]=1[O-]>CN(C=O)C.C(OCC)(=O)C>[N:22]12[CH2:27][CH2:26][CH:25]([CH2:24][CH2:23]1)[C@@H:20]([O:19][C:17](=[O:18])[NH:16][C@H:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][C:6]3[N:2]([CH3:1])[N:3]=[C:4]([C:34](=[O:35])[NH:51][CH2:50][CH2:49][CH2:48][CH:47]([O:46][CH2:44][CH3:45])[O:52][CH2:53][CH3:54])[CH:5]=3)[CH:10]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:21]2

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 806724,4-DiethoxybutylamineHCID 867208301-methyl-5((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)-methyl)-1H-pyrazole-3-carboxylic acidHCID 178526252HCID 178526252, Verbindung

Produkt 1

HCID 90211958(R)-Quinuclidin-3-yl ((S)-(3-((3-((4,4-diethoxybutyl)carbamoyl)-1-methyl-1H-pyrazol-5-yl)methoxy)phenyl)(phenyl)methyl)carbamateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-methyl-5-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)-1H-pyrazole-3-carboxylic acid (0.30 g, 0.61 mmol) in DMF (6 mL) was added triethylamine (0.2 mL, 1.53 mmol), 4-aminobutyraldehyde diethyl acetal (0.20 mL, 1.22 mmol), EDCI (0.18 g, 0.91 mmol) and 2-hydroxypyridine-N-oxide (0.09 g, 0.91 mmol). The reaction mixture stirred at RT for 90 h. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium hydrogen carbonate, brine, dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure to afford the crude target material (0.22 g, 57%) which was used directly without further purification.

Aufarbeitung

  1. washwashed with saturated sodium hydrogen carbonate, brine
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. customthe solvent evaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f9f2c2bc164e4d6bbfb164213a227c6c
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987299B2

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