Diisopropylethylamine → HCID 67229453, Verbindung

HRID 1844322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844322
Cl.Cl.[C@H:3]12[CH2:9][C@H:6]([NH:7][CH2:8]1)[CH2:5][N:4]2[C:10]([C@@:12]1([C:26]2([OH:30])[CH2:29][CH2:28][CH2:27]2)[CH2:16][CH2:15][C@@H:14]([NH:17][C@@H:18]2[C@H:23]([O:24][CH3:25])[CH2:22][O:21][CH2:20][CH2:19]2)[CH2:13]1)=[O:11].Cl[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[N:33]=1.C(N(C(C)C)CC)(C)C>CS(C)=O>[OH:30][C:26]1([C@:12]2([C:10]([N:4]3[CH2:5][C@@H:6]4[CH2:9][C@H:3]3[CH2:8][N:7]4[C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[N:33]=3)=[O:11])[CH2:16][CH2:15][C@@H:14]([NH:17][C@@H:18]3[C@H:23]([O:24][CH3:25])[CH2:22][O:21][CH2:20][CH2:19]3)[CH2:13]2)[CH2:29][CH2:28][CH2:27]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 6023342-Chloro-6-(trifluoromethyl)pyridineHCID 67228799HCID 67228799, Verbindung

Produkt 1

HCID 67229453HCID 67229453, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 93 mg (0.20 mmol) of 1,5-anhydro-2,3-dideoxy-3-[{(1R,3S)-3-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylcarbonyl]-3-(1-hydroxycyclobutyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol dihydrochloride, 91 mg (0.49 mmol) of 2-chloro-6-trifluoromethylpyridine, and 0.14 mL (0.80 mmol) of diisopropylethylamine in 0.5 mL of DMSO was heated at 80 C for 18 h, then cooled and partitioned between ethyl acetate and water. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The crude material was purified by preparative RP-HPLC using as the mobile phase acetonitrile-water containing 0.05% TFA. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46-2.52 (m, 16H) 3.26-3.54 (m, 8H) 3.53-3.92 (m, 4H) 4.02 (dd, J=11.8, 4.3 Hz, 1H) 4.22 (d, J=13.0 Hz, 1H) 5.01 (d, J=14.3 Hz, 2H) 6.47 (d, J=8.5 Hz, 1H) 6.93 (d, J=7.5 Hz, 1H) 7.56 (t, J=8.0 Hz, 1H). HRMS calculated for C27H37N4O4F3: 539.2845. found: 539.2894

Aufarbeitung

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by preparative RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c37d6f2a514d43848dd5d4425f78d7d8
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946413B2

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