Azetidine → 5-(Azetidin-1-ylsulfonyl)-2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole

HRID 1435413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435413
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21](Cl)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:25]1[CH2:28][CH2:27][CH2:26]1>CN(C1C=CN=CC=1)C.CC#N>[N:25]1([S:21]([C:19]2[CH:18]=[CH:17][C:8]3[N:9]([CH2:10][CH:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6][C:7]=3[CH:20]=2)(=[O:23])=[O:22])[CH2:28][CH2:27][CH2:26]1

Komponenten

5

Edukt 2

HCID 10422AzetidineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Produkt 1

HCID 236593015-(Azetidin-1-ylsulfonyl)-2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (76 mg, 0.20 mmol), azetidine (34 uL, 26 mg, 0.50 mmol) and DMAP (82 mg, 0.67 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:2) on silica gel to give 37 mg (46% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.52-1.65 (m, 4 H), 1.68 (s, 9 H), 1.99-2.13 (m, 2 H), 2.32-2.47 (m, 1 H), 3.32-3.43 (m, 2 H), 3.74-3.84 (m, 4 H), 3.90-4.01 (m, 2 H), 4.54 (d, J=7.42 Hz, 2 H), 7.92 (dd, J=8.79, 1.56 Hz, 1 H), 8.09 (d, J=8.79 Hz, 1 H), 8.15 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=392.0; Anal. Calcd for C20H29N3O3S+1.20 TFA+0.40 EtOAc+0.1H2O (556.60): C, 50.93; H, 5.94; N, 7.55. Found: C, 50.98; H, 5.68; N, 7.50.

Aufarbeitung

  1. customThe crude product was purified by MPLC

Quellen und Nachweise

ORD-Eintrag
ord-7ee95019ea854ca28dfcdeb38cb719e6
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615642B2

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