(2,6-Dichloropyridin-4-yl)methanol → {2-Chloro-6-[1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-ylamino]-pyridin-4-yl}-methanol

HRID 913080Notes

Reaction equation

HRID 913080 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.[Cl:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]2)=[CH:14][C:13]=1[O:26][CH2:27][CH3:28]>CN(C=O)C>[Cl:10][C:4]1[CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=[C:2]([NH:23][CH:20]2[CH2:21][CH2:22][N:17]([CH2:16][C:15]3[CH:24]=[CH:25][C:12]([Cl:11])=[C:13]([O:26][CH2:27][CH3:28])[CH:14]=3)[CH2:18][CH2:19]2)[N:3]=1

Participants

4

Reactant 2

HCID 2794840(2,6-Dichloropyridin-4-yl)methanolHCID 592103771-(4-Chloro-3-ethoxybenzyl)piperidin-4-ylamine2×

Product 1

HCID 24855125{2-Chloro-6-[1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-ylamino]-pyridin-4-yl}-methanolYield 4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2,6-dichloro-pyridin-4-yl)-methanol (44.5 mg, 0.25 mmol, 1.25 equiv; commercially available) and 1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-ylamine (53.8 mg, 0.20 mmol, 1.2 equiv; intermediate A2) in DMF (2.0 mL) was heated by microwave irradiation to 220° C. for 1 h. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 3.2 mg (4%) of the title compound. MS (ISP): 410.3 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase
  3. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-cd40fdc722ac4340ad2e9ad5e101a26f
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

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