Sulfuric Acid → HCID 71544570, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2O[C:10]([C:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)(O)[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.O[S:23](O)(=O)=O.[OH-:27].[Na+].[CH3:29][C:30]#[N:31]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:23][C:10]([C:13]([NH:31][C:30](=[O:27])[CH3:29])([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 90 °C
Procedure
A stirred solution of 1-(2-(4-fluorophenyl)thiazol-5-yl)-1-(pyridin-4-yl)ethanol (Example 7) (0.450 g, 1.50 mmol) in MeCN (2.25 mL) was heated at 90° C. and then conc. H2SO4 (0.58 mL) in MeCN (2.25 mL) was added. The reaction mixture was stirred at 90° C. for 3 hrs, then it was cooled to room temperature and ice was added. The resulting mixture was neutralized with 10% NaOH solution, extracted with ethyl acetate (3×250 mL), and the combined organic layers were concentrated under vacuum. The crude product obtained was purified by column chromatography using silica gel (100-200 mesh) and MeOH:CH2Cl2 (3:7) as eluent to afford 95 mg (19%) of N-(1-(2-(4-fluorophenyl)thiazol-5-yl)-1-(pyridin-4-yl)ethyl)acetamide as a colorless solid. 1H NMR (400 MHz, DMSO-d6): δ 8.72 (br s, 1H), 8.48 (dd, 2H, J=4.4, 1.6 Hz), 7.93 (m, 2H), 7.80 (s, 1H), 7.29 (t, 2H, J=8.8 Hz), 7.20 (dd, 2H, J=4.4, 1.6 Hz); 1.97 (s, 3H), 1.90 (s, 3H), LC-MS m/z calculated for [M+H]+ 342.10. found 342.1.
Workup
- temperatureit was cooled to room temperature
- additionice was added
- extractionextracted with ethyl acetate (3×250 mL)
- concentrationthe combined organic layers were concentrated under vacuum
- customThe crude product obtained
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-ab9aeeb5e0c84471ac800daad6f08170
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266873B2
Reaction notes
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