Dimethylformamide → 6-(6-Chloropyrimidin-4-yloxy)naphthalene-1-carbonyl chloride

HRID 1094520Notes

Reaction equation

HRID 1094520 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Cl:7][C:8]1[N:13]=[CH:12][N:11]=[C:10]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)C(C(O)=O)=[CH:20][CH:19]=[CH:18]3)[CH:9]=1.CN(C=O)C>C(Cl)Cl>[Cl:7][C:8]1[N:13]=[CH:12][N:11]=[C:10]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:1]([C:2]([Cl:4])=[O:3])=[CH:20][CH:19]=[CH:18]3)[CH:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 248238946-(6-Chloropyrimidin-4-yloxy)-1-naphthoic acid

Product 1

HCID 574551736-(6-Chloropyrimidin-4-yloxy)naphthalene-1-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 571 μl (6.66 mMol) oxalyl chloride in 15 ml CH2Cl2 is added to an ice-cooled solution of 1 g (3.33 mMol) 6-(6-chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (preparation see WO 2006/59234; Step 25.1) and 10 μl DMF in 30 ml CH2Cl2. The reaction mixture is stirred at room temperature for 1 h. The solvent is then evaporated off under reduced pressure to afford the title compound as a brown solid, which is used directly without further purification.

Workup

  1. customThe solvent is then evaporated off under reduced pressure

Sources & evidence

ORD record
ord-b24ac829663e483fac4883f95dd9ac02
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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