Potassium Carbonate → HCID 10311043, compound

HRID 895696Notes

Reaction equation

HRID 895696 reaction equation
[CH3:1][C:2]1[CH2:3][CH2:4][NH:5][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[C:7]=1[CH3:8].Cl[CH2:17][C:18]([N:20]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[F:37])[CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)=[O:19].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:1][C:2]1[CH2:3][CH2:4][N:5]([CH2:17][C:18]([N:20]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[CH:21]2[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22]2)=[O:19])[CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22380829HCID 22380829, compoundHCID 22380835HCID 22380835, compound

Product 1

HCID 10311043HCID 10311043, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4,5-dimethyl-6-o-tolyl-1,2,3,6-tetrahydro-pyridine (170 mg; 0.85 mmol), 2-chloro-N-(2-fluoro-benzyl)-N-indan-2-yl-acetamide (403 mg; 1.27 mmol) and K2CO3 (587 mg; 4.25 mmol), and acetonitrile (20 ml) is stirred at 80° C. for 20 hours. The reaction mixture is filtered, the insolubles are washed with ethyl acetate, and the filtrate is concentrated in vacuo. The residue is purified by flash chromatography over silica gel (elution with hexanes/ethyl acetate 3:1) to give the product (Compound 13) as an oil. LC-MS [MH+] 483.25, RT=2.69 min.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe insolubles are washed with ethyl acetate
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe residue is purified by flash chromatography over silica gel (elution with hexanes/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-10aac3b8162742e283d55a4f78ad3793
Source dataset
uspto-grants-2005_07
Patent number
US06916830B2

Reaction notes

Loading…