2-(Pyridin-3-yloxy)ethan-1-ol → PRX933 hydrochloride

HRID 493322Notes

Reaction equation

HRID 493322 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][OH:10])[CH:2]=1.[Cl:11][C:12]1[C:13]([N:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][C@H:19]2[CH3:31])=[N:14][CH:15]=[CH:16][N:17]=1>>[ClH:11].[CH3:31][C@@H:19]1[CH2:20][NH:21][CH2:22][CH2:23][N:18]1[C:13]1[C:12]([O:10][CH2:9][CH2:8][O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:17][CH:16]=[CH:15][N:14]=1

Participants

3

Reactant 2

HCID 219089972-(Pyridin-3-yloxy)ethan-1-olHCID 86591091(R)-tert-butyl 4-(3-chloropyrazin-2-yl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 131723551PRX933 hydrochloride

Procedure

The title compound was prepared starting from 2-(3-pyridyloxy)ethanol (from Example 150, Step 1) and 3-chloro-2-[4-tert-butoxycarbonyl-(2R)-methyl-1-piperazinyl]pyrazine (from Example 172, Step 2). The pure free base was precipitated as its hydrochloride salt with HCl/ether to give the title compound as white crystals: yield 31%; mp 180-183° C.; HRMS m/z calcd for C16H21N5O2 (M)+ 315.1695, found 315.1689. Anal. (C16H21N5O2.1.33HCl) C, H, N.

Workup

  1. customThe title compound was prepared
  2. customThe pure free base was precipitated as its hydrochloride salt with HCl/ether

Sources & evidence

ORD record
ord-2807f886d0d144e3ba31dceaa4a8ea9a
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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