Dimethylformamide → HCID 178429779, compound

To a solution of cis-4-(4-iodo-5-methyl-1H-pyrazol-1-yl)cyclohexanol (400.0 mg, 1.306 mmol), triethylamine (0.5463 mL, 3.920 mmol) and DCM (10 mL, 200 mmol) was added methanesulfonyl chloride (0.2022 mL, 2.613 mmol), and the reaction was stirred at rt for 2 h. The material was extracted with DCM and water, which was titrated to pH=5. The organic layer was concentrated in vacuo, redissolved in DMF (5 mL, 60 mmol), and sodium azide (169.9 mg, 2.613 mmol) was added. The mixture was heated to 90° C. for 3 h. The material was extracted with EtOAc, and washed with water (2×). The organic layer was concentrated in vacuo, redissolved in 1,4-dioxane (5 mL, 60 mmol), and PPh3 (514.0 mg, 1.960 mmol) was added. The mixture was heated to 70° C. for 3 h. The solvent was removed in vacuo, and the material was extracted with DCM and water, which was titrated to pH=2. The organic layer was discarded, more DCM was added, and the aqueous layer was titrated to pH=9. The organic layer was concentrated in vacuo to afford the title compound as a light yellow solid. MS (ES+): m/z=306.04 (100) [MH+]. HPLC: tR=0.89 min (polar—3 min, UPLC-ACQUITY).

1. extractionThe material was extracted with DCM and water, which
2. concentrationThe organic layer was concentrated in vacuo
3. temperatureThe mixture was heated to 90° C. for 3 h
4. extractionThe material was extracted with EtOAc
5. washwashed with water (2×)
6. concentrationThe organic layer was concentrated in vacuo
7. temperatureThe mixture was heated to 70° C. for 3 h
8. customThe solvent was removed in vacuo
9. extractionthe material was extracted with DCM and water, which
10. additionmore DCM was added
11. concentrationThe organic layer was concentrated in vacuo

ORD record

ord-2cdf8865730440639f4f77ffcc5ae837

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445510B2