2,6-Lutidine → HCID 178433630, compound

HRID 2271116Notes

Reaction equation

HRID 2271116 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:27](=[O:28])[C:11]3=[CH:12][NH:13][C:14]([CH3:26])=[C:15]([C:16]4[CH:21]=[CH:20][C:19]([C:22]#[C:23][CH2:24]O)=[CH:18][CH:17]=4)[C:10]3=[N:9]2)=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.[Cl-].[Li+].CS([Cl:43])(=O)=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:27](=[O:28])[C:11]3=[CH:12][NH:13][C:14]([CH3:26])=[C:15]([C:16]4[CH:21]=[CH:20][C:19]([C:22]#[C:23][CH2:24][Cl:43])=[CH:18][CH:17]=4)[C:10]3=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 178433631HCID 178433631, compound

Product 1

HCID 178433630HCID 178433630, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of Example 68 (0.6 g, 1.5 mmol), 2,6-lutidine (0.72 ml, 6.2 mmol) and lithium chloride (0.262 g, 6.2 mmol) in N,N-dimethylformamide (6 ml) at 0° C. was added methanesulphonyl chloride (0.36 ml, 4.6 mmol) dropwise and the solution allowed to warm to ambient temperature with stirring for 7 hours. The solvent was removed in vacuo and the crude product purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2) to give the product as a yellow solid (0.463 g, 74%). 1H NMR (360 MHz, DMSO-d6) δ12.49 (1H, br s), 8.59 (1H, s), 8.13 (2H, d, J 9.0 Hz), 7.59 (4H, m), 7.41 (2H, d, J 9.0 Hz), 4.75 (2H, s), 2.26 (3H, s); MS (ES+) m/z 408/410/412 [MH]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-96b311e36ca54ce19d3437b803fad983
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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