HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → methyl N-[[2-chloro-5-[1-(3,4-dihydro-3-oxo-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | methyl N-[[2-chloro-5-(1-spiro[2H-1-benzopyran-3(4H), 2'-[1,3]dioxolan]-6-yl-1H-pyrazol-3-yl)phenyl]methyl]carbamate | HCID 67151202 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | methyl N-[[2-chloro-5-[1-(3,4-dihydro-3-oxo-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate | HCID 67151129 | 68% |
Reaction Steps
To a solution of methyl N-[[2-chloro-5-(1-spiro[2H-1-benzopyran-3(4H), 2′-[1,3]dioxolan]-6-yl-1H-pyrazol-3-yl)phenyl]methyl]carbamate (i.e. the product of Example 9, Step B) (150 mg, 0.32 mmol) in acetone (15 mL) was added 3N HCl (4.5 mL). The reaction mixture was heated at 85° C. for 16 hrs when TLC analysis (50% ethyl acetate/pet ether) showed completion of reaction. The reaction mixture was cooled and the solvent was concentrated under vacuum. The resultant residue was partitioned between water and ethyl acetate. The organic phase was washed with water, brine, dried over Na2SO4 and concentrated under vacuum to give the title compound, a compound of the present invention, (90 mg, 68% yield) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08921360B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-52ac1ee65a0840afae2eca54cb4fe130 |
| Source note | uspto-grants-2014_12 |