1-(2-(4-Iodophenoxy)ethyl)-4-methylpiperidine → (5-(4-Chlorophenyl)-2-{4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylethynyl}pyridin-3-yl)methylamine

HRID 734872Notes

Reaction equation

HRID 734872 reaction equation
I[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH3:15])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[C:27]([CH2:33][NH2:34])[C:28]([C:31]#[CH:32])=[N:29][CH:30]=2)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[C:27]([CH2:33][NH2:34])[C:28]([C:31]#[C:32][C:2]3[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][N:9]4[CH2:14][CH2:13][CH:12]([CH3:15])[CH2:11][CH2:10]4)=[CH:4][CH:3]=3)=[N:29][CH:30]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 690610171-(2-(4-Iodophenoxy)ethyl)-4-methylpiperidineHCID 86601138[5-(4-Chlorophenyl)-2-ethynylpyridin-3-yl]methylamine

Product 1

HCID 69063344(5-(4-Chlorophenyl)-2-{4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylethynyl}pyridin-3-yl)methylamine

Procedure

The product was prepared analogously to Example 7.1e starting from 1-[2-(4-iodophenoxy)ethyl]-4-methylpiperidine and [5-(4-chlorophenyl)-2-ethynylpyridin-3-yl]methylamine. Yield: 70 mg (21% of theoretical); C28H30ClN3O (M=460.010); calc.: molpeak (M+H)+:460/462 (Cl); found: molpeak (M+H)+:460/462 (Cl); HPLC-MS: 5.30 minutes (method D).

Workup

  1. customThe product was prepared analogously to Example 7.1e
  2. custom5.30 minutes (method D)

Sources & evidence

ORD record
ord-707876839b944af5837fa74e9fff8fe3
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

Loading…