Hydrochloric Acid → HCID 59529787, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][N:10]2C(OC(C)(C)C)=O)=[O:8])=[CH:3][CH:2]=1.Cl.CCN(C(C)C)C(C)C.[CH3:32][N:33]1[CH:37]=[C:36]([S:38](Cl)(=[O:40])=[O:39])[N:35]=[CH:34]1>O1CCOCC1>[CH3:32][N:33]1[CH:37]=[C:36]([S:38]([N:12]2[CH2:13][CH2:14][CH:9]([C:7]([C:4]3[CH:3]=[CH:2][CH:1]=[CH:6][N:5]=3)=[O:8])[CH2:10][CH2:11]2)(=[O:40])=[O:39])[N:35]=[CH:34]1Participants
Procedure
To a solution of 6 (950 mg, 3.27 mmol) in 1,4-dioxane (5 mL) was added 4 N HCl in dioxane (10 mL) and stirred for 1 h. The solvent was removed under vacuum. The residue was dissolved in CH2Cl2 (10 mL), added DIPEA (1.94 mL, 10.8 mmol) and 1-methylimidazole-4-sulfonyl chloride (589 mg, 3.27 mmol). The reaction was stirred for 18 h at room temperature. The reaction mixture was washed with 2 N NaOH (10 mL), dried over MgSO4 and concentrated under vacuum to afford 7 as a light orange oil (920 mg, 84%); 1H-nmr (400 MHz, CDCl3) δ 8.63 (d, J=5.0 Hz, 1H), 8.02 (d, J=8.0 Hz, 1H), 7.85 (td, J=8.0, 1.5 Hz, 1H), 7.50 (s, 1H), 7.48 (dd, J=8.0, 1.5 Hz, 1H), 7.44 (s, 1H), 4.00-3.82 (m, 3H), 3.77 (s, 3H), 2.86 (t, J=11.0 Hz, 2H), 2.04-1.96 (m, 2H), 1.91-1.78 (m, 2H); m/z 335.1 [M+H].
Workup
- customThe solvent was removed under vacuum
- dissolutionThe residue was dissolved in CH2Cl2 (10 mL)
- stirringThe reaction was stirred for 18 h at room temperature
- washThe reaction mixture was washed with 2 N NaOH (10 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-114390384d2143b7bae5f4a3c275cfca
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08436019B2
Reaction notes
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