Hydrochloric Acid → HCID 57941415, compound
Reaction equation
C(N(CC)CC)C.C(O[C:13]([NH:15][N:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=1[F:25])C)=O)(C)(C)C.[CH3:26][C@:27]12[C:33]([CH3:35])([CH3:34])[C@H:30]([CH2:31][CH2:32]1)[CH:29]([C:36](Cl)=[O:37])[C:28]2=O.Cl.O1CCOCC1>ClCCCl>[F:25][C:19]1[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:18]=1[N:16]1[C:36](=[O:37])[C:29]2[C@@H:30]3[C:33]([CH3:35])([CH3:34])[C@@:27]([CH3:26])([CH2:32][CH2:31]3)[C:28]=2[N:15]1[CH3:13]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Triethylamine (1 mL, 7.2 mmol) was added dropwise to a solution of N′-(2,3-difluoro-phenyl)-N′-methyl-hydrazinecarboxylic acid tert-butyl ester (360 mg, 1.4 mmol) in 1,2-dichloroethane (6 mL) over 1 min. The reaction mixture was stirred for 5 min and then a solution of (1R,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl chloride (Intermediate 20; 800 mg, 3.72 mmol) in 1,2-dichloroethane (14 mL) was added over 2 min. The reaction mixture was heated in an oil bath at 50° C. for 1 h. The solution was allowed to cool and a solution of HCl in dioxane (4 M; 6 mL, 24 mmol) was added and the mixture was heated at reflux for 1.5 h and then allowed to cool to room temperature. The solvent was evaporated and the residue was purified by preparative HPLC and dried under high vacuum to give (4S,7R)-2-(2,3-difluoro-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (129 mg, 29%) as a white solid. ES(+)-MS (M+H) 319.
Workup
- temperatureto cool
- temperaturethe mixture was heated
- temperatureat reflux for 1.5 h
- temperatureto cool to room temperature
- customThe solvent was evaporated
- customthe residue was purified by preparative HPLC
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-5fb7424a399a49978c6464307a90720d
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622492B2
Reaction notes
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