HCID 69251257, compound → HCID 59701475, compound

HRID 902638Notes

Reaction equation

HRID 902638 reaction equation
[Cl:1][C:2]1[C:37]([C:38]([F:41])([F:40])[F:39])=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][N:5]([CH2:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([N+:17]([O-])=O)[CH:11]=1>[Pd].Cl.CCOCC>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:4][C:3]2[CH:34]=[CH:35][CH:36]=[C:37]([C:38]([F:40])([F:41])[F:39])[C:2]=2[Cl:1])[CH2:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:11][C:12]=1[NH2:17]

Participants

4

Reactant 1

HCID 69251257HCID 69251257, compound

Product 1

HCID 59701475HCID 59701475, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10953452Ether hydrochlorideSolvent

Procedure

(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-[3-(4-chloro-3-nitro-phenoxy)-propyl]-amine (400 mg, 0.66 mmol) was hydrogenated over 10% Pd/C (40 mg) at 60 psi at room temperature in the presence of 1N HCl-Et2O (10 ml). After 24 h, the reaction mixture was filtered and concentrated in vacuo to give a heavy oil. HPLC purification of the crude amine (Phenomonex Luna Combi HTS, 5 micron C18, 275 mm×30 mm, 10% CH3CN— water gradient to 95% CH3CN) afforded the title compound as an oil. Treatment of the free base with 1N HCl-Et2O (excess), followed by filtration and isolation of the resulting precipitate gave the title compound as a brown solid, 18.5 mg (4.3%). MS (ESI) 572.5 (M+).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto give a heavy oil
  4. customHPLC purification of the crude amine (Phenomonex Luna Combi HTS, 5 micron C18, 275 mm×30 mm, 10% CH3CN— water gradient to 95% CH3CN)

Sources & evidence

ORD record
ord-4caa8da2be294622b74682518db63313
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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