Hydrochloric Acid → HCID 50896787, compound
Reaction equation
COC1C=CC(C[N:8]2[C:12]([CH2:13][NH:14]C(=O)OC(C)(C)C)=[CH:11][C:10]([C:22]([F:25])([F:24])[F:23])=[N:9]2)=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].C(OCC)(=O)C.CCCCCC.Cl>C1(C)C=CC=CC=1>[F:25][C:22]([F:23])([F:24])[C:10]1[CH:11]=[C:12]([CH2:13][NH2:14])[NH:8][N:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
To a stirred solution of tert-butyl (1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate (20 g, 0.052 mol) in toluene (300 mL) cooled to 0° C. was added aluminum chloride (17.34 g, 0.129 mol) portion wise for 30 min. The reaction mixture was slowly heated to 50-60° C. and allowed to stir for 2 h at the same temperature. Progress of the reaction was monitored by TLC (20% ethyl acetate/hexane, Rf˜0.1). On completion of the reaction, the reaction contents were treated with diluted HCl, ice cold water (300 mL) was added and the mixture was extracted with ethyl acetate (2×100 mL). The aqueous layer was basified with sodium hydroxide solution and extracted with ethyl acetate and dried over sodium sulfate and concentrated under reduced pressure to give (3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine as a brown colored solid (4.6 g, crude). The crude product obtained was used directly for the next step.
Workup
- customOn completion of the reaction
- customthe reaction contents
- additionwas added
- extractionthe mixture was extracted with ethyl acetate (2×100 mL)
- extractionextracted with ethyl acetate
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d5c90ef364c441db9cafe5ad923a1415
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946204B2
Reaction notes
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