2-Chlorobenzyl chloroformate → HCID 11584392, Verbindung

HRID 1432428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432428
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:3].[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]3[N:26]=[C:25]([CH:27]4[CH2:32][CH2:31][N:30](S(CC5C=CC=CC=5)(=O)=O)[CH2:29][CH2:28]4)[NH:24][C:23]=3[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=3)=[CH:21][C:16]=2[O:15][CH2:14]1>C1COCC1.C(=O)(O)[O-].[Na+]>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][O:4][C:2]([N:30]1[CH2:29][CH2:28][CH:27]([C:25]2[NH:24][C:23]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=3)=[C:22]([C:20]3[CH:19]=[CH:18][C:17]4[O:13][CH2:14][O:15][C:16]=4[CH:21]=3)[N:26]=2)[CH2:32][CH2:31]1)=[O:3]

Komponenten

5

Edukt 2

HCID 40723422-Chlorobenzyl chloroformateHCID 10345947HCID 10345947, Verbindung

Produkt 1

HCID 11584392HCID 11584392, VerbindungAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

2-Chlorobenzyl chloroformate (0.011 mL, 0.070 mmol) was added to a solution of 2-(5-benzo[1,3]dioxol-5-yl-2-piperidin-4-yl-3H-imidazol-4-yl)-pyridine (0.021 g, 0.059 mmol; prepared as described in Example 11) in a mixture of THF (3 mL) and 2 M sodium bicarbonate aqueous solution (0.3 mL). The mixture was stirred at room temperature for 2 hours. Mixture was partitioned between ethyl acetate and water. The organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated. HPLC purification eluting with acetonitrile:water gave 0.026 g (70%) of the title compound as a yellow solid. MS (ESP+) m/z 517.03 (M+1). 1H NMR (400 MHz, CDCl3) δ 8.60 (m, 1H), 7.81 (m, 1H), 7.60 (d, 1H, J=8.2 Hz), 7.39 (m, 3H), 7.27 (m, 2H), 7.07 (dd, 1H, J=8.1, 1.8 Hz), 6.99 (d, 1H, J=1.8 Hz), 6.90 (d, 1H, J=8.1 Hz), 6.05 (s, 2H), 5.24 (s, 2H), 4.36 (m, 2H), 3.48 (m, 1H), 2.98 (m, 2H), 2.17 (m, 2H), 1.86 (m, 2H).

Aufarbeitung

  1. customMixture was partitioned between ethyl acetate and water
  2. washThe organic solution was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customHPLC purification
  7. washeluting with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-c4025974f2e744aaa92e95372d3a30cf
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612094B2

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