Hydrochloric Acid → 4-(Amino(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methyl)-3-methylbenzonitrile hydrochloride
Reaction equation
[ClH:1].C(C1C=CC([N:10]([CH2:18][C:19]2[C:24](=[O:25])[CH2:23][CH2:22][CH2:21][C:20]=2[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)C(=O)OC(C)(C)C)=C(C)C=1)#N.O1[CH2:43][CH2:42]OCC1>>[ClH:1].[NH2:10][CH:18]([C:19]1[C:24](=[O:25])[CH2:23][CH2:22][CH2:21][C:20]=1[NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:36])[F:35])[CH:28]=1)[C:22]1[CH:21]=[CH:20][C:19]([C:18]#[N:10])=[CH:24][C:42]=1[CH3:43]Participants
4
Reactant 3
Product 1
Procedure
Hydrogen chloride (4 M in 1,4-dioxane, 5.50 mL, 22.0 mmol) is added to a solution of tert-butyl (4-cyano-2-methylphenyl)(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methylcarbamate (intermediate 51, 1.57 g, 3.14 mmol) in 1,4-dioxane (10 mL), and the mixture is stirred at room temperature over night. All volatiles are removed under reduced pressure, and the residue is treated with tert-butyl methyl ether. The precipitate is filtered and dried. Yield: 1.18 g; ESI mass spectrum [M+H]+=400; Retention time HPLC: 0.56 min (X012_S01).
Workup
- customAll volatiles are removed under reduced pressure
- additionthe residue is treated with tert-butyl methyl ether
- filtrationThe precipitate is filtered
- customdried
- custom0.56 min (X012_S01)
Sources & evidence
- ORD record
- ord-5a9a8dee9e8f495682213880d968047c
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115093B2
Reaction notes
Loading…