2,4,6-Trimethylpyridine → N-(4-Chlorobenzyl)-2-(chloromethyl)-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23642Notes

Reaction equation

HRID 23642 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:30])[C:12]3[S:19][C:18]([CH2:20]O)=[C:17]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.CS([Cl:46])(=O)=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:30])[C:12]3[S:19][C:18]([CH2:20][Cl:46])=[C:17]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 22574330N-(4-Chlorobenzyl)-2-(hydroxymethyl)-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 22574390N-(4-Chlorobenzyl)-2-(chloromethyl)-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.), stirred solution of 426 mg of N-(4-chlorobenzyl)-2-(hydroxymethyl)-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide and 0.46 mL of 2,4,6-collidine in 4 mL of dry DMF is added 0.17 mL of methanesulfonyl chloride. The ice bath is removed and the mixture is allowed to stir for 18 h, then is diluted slowly with water to a volume of 25 mL. The resulting solid is filtered, washed well with water, and dried in vacuo to furnish 429 mg of the title compound as a brown solid.

Workup

  1. customThe ice bath is removed
  2. additionis diluted slowly with water to a volume of 25 mL
  3. filtrationThe resulting solid is filtered
  4. washwashed well with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-7ed2312dfcac4c3a8e367cbfdb3be246
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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