Hydrochloric Acid → 1-(1-methyl-1H-imidazol-4-ylsulfonyl)azetidine-3-carbonitrile

To a solution of 1-N-Boc-3-cyanoazetidine (5.0 g, 27.5 mmol) in 1,4-dioxane (50 mL) was added 4 N HCl (50 mL) and stirred for 2 h. The reaction was concentrated under vacuum. The residue was dissolved in CH2Cl2 (60 mL) and DIPEA (10.6 mL, 60.4 mmol) and added 1-methylimidazole-4-sulfonyl chloride (4.94 g, 27.5 mmol) and stirred at room temperature for 20 h. The reaction mixture was washed with 2 N NaOH (50 mL), dried over MgSO4 and concentrated under vacuum to afford 8 as a white crystalline solid (4.97 g, 80%); 1H-nmr (300 MHz, CDCl3) δ 7.06 (s, 1H), 7.56 (s, 1H), 4.27-4.19 (m, 4H), 3.82 (s, 3H), 3.43-3.31 (m, 1H); LC-MS (214) 99%, 0.93 min, m/z 227.1 (M+H).

1. concentrationThe reaction was concentrated under vacuum
2. dissolutionThe residue was dissolved in CH2Cl2 (60 mL)
3. stirringstirred at room temperature for 20 h
4. washThe reaction mixture was washed with 2 N NaOH (50 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated under vacuum

ORDレコード

ord-813792d6910d47c09ead3188c7288b7d

出典データセット

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08207155B2