Hydrochloric Acid → 4-(Amino(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methyl)-3-chloro-benzonitrile hydrochloride

HRID 517223Notes

Reaction equation

HRID 517223 reaction equation
[ClH:1].[Cl:2]C1C=C(C#N)C=CC=1[N:11]([CH2:19][C:20]1[C:25](=[O:26])[CH2:24][CH2:23][CH2:22][C:21]=1[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=1)C(=O)OC(C)(C)C>O1CCOCC1>[ClH:2].[NH2:11][CH:19]([C:20]1[C:25](=[O:26])[CH2:24][CH2:23][CH2:22][C:21]=1[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[CH:29]=1)[C:23]1[CH:24]=[CH:25][C:20]([C:19]#[N:11])=[CH:21][C:22]=1[Cl:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86732342tert-Butyl (2-Chloro-4-cyanophenyl)(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methylcarbamate2×

Product 1

HCID 867323434-(Amino(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methyl)-3-chloro-benzonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride (4 M in 1,4-dioxane, 4.0 mL, 16.2 mmol) is added to a solution of tert-butyl (2-chloro-4-cyanophenyl)(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methylcarbamate (intermediate 53, 1.05 g, 2.02 mmol) in 1,4-dioxane (5 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: 690 mg; ESI mass spectrum [M+H]+=420; Retention time HPLC: 0.57 min (X012_S01).

Workup

  1. customAll volatiles are removed under reduced pressure
  2. additionthe residue is treated with tert-butyl methyl ether
  3. filtrationThe precipitate is filtered
  4. customdried
  5. custom0.57 min (X012_S01)

Sources & evidence

ORD record
ord-f4d1d515fc784e79b5d5966237fd667c
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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