Aniline → HCID 178463271, compound

HRID 1914657Notes

Reaction equation

HRID 1914657 reaction equation
[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:23])[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=2[Cl:22])[CH2:6][CH2:5]1)(=O)[CH3:2].[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C=O)C.Cl[SiH](Cl)Cl>C(Cl)Cl>[Cl:22][C:13]1[CH:14]=[CH:15][C:16]([C:18]([F:21])([F:20])[F:19])=[CH:17][C:12]=1[C:11]([NH:10][C@H:7]1[CH2:8][CH2:9][C@H:4]([CH:1]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:2])[CH2:5][CH2:6]1)=[O:23]

Participants

6

Reactant 4

HCID 6115AnilineHCID 6228Dimethylformamide2×HCID 24811Trichlorosilane2×HCID 178468179HCID 178468179, compound

Product 1

HCID 178463271HCID 178463271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Trans-N-(4-acetylcyclohexyl)-2-chloro-5-(trifluoromethyl)-benzamide (200 mg, 0.57 mmol) and aniline (54 mg, 0.57 mmol) in DCM (10 mL) is added DMF (0.1 mL) followed by trichlorosilane (78 mg, 0.57 mmol). After stirring at room temperature for 1 hour, further trichlorosilane (5×78 mg, 5×0.57 mmol) is added at 1 hour intervals for the next 5 hours. Further DMF (0.1 mL) was then added and the mixture is stirred at room temperature overnight. The colourless solid that is formed is recovered by filtration, washed successively with water and then EtOAc and dried. [MH+425.38]. The racemic mixture was separated by supercritical fluid chromatography on chiral stationary phase analogously to that reported for Example 1.37.

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. customThe colourless solid that is formed
  3. filtrationis recovered by filtration
  4. washwashed successively with water
  5. dry with materialEtOAc and dried
  6. customThe racemic mixture was separated by supercritical fluid chromatography on chiral stationary phase analogously to

Sources & evidence

ORD record
ord-47e6ba2efd8149db8c4d10484fed7c69
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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