Aniline → HCID 178463271, compound

HRID 2391019Notes

Reaction equation

HRID 2391019 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-63110cfd55424349a5948e71293c1b13
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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