Acetic Acid → N-(4-Chlorobenzyl)-2-(hydroxymethyl)-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23636Notes

Reaction equation

HRID 23636 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:28])[C:12]3[S:19][C:18]([CH:20]=[O:21])=[C:17]([CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:28])[C:12]3[S:19][C:18]([CH2:20][OH:21])=[C:17]([CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 22574380N-(4-Chlorobenzyl)-2-formyl-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 22574407N-(4-Chlorobenzyl)-2-(hydroxymethyl)-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 102.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.), stirred solution of 1.05 g of N-(4-chlorobenzyl)-2-formyl-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 20 mL of CH2Cl2 is added 0.67 mL of acetic acid and 1.5 g of sodium triacetoxyborohydride. The mixture is allowed to warm to room temperature and stirred for 2 h, then partitioned between CH2Cl2 and aqueous NaHCO3. The organic phase is dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica using 2.5-4% MeOH in CH2Cl2 affords 1.08 g (100%) of the title compound as a yellow crystalline solid. Recrystallization from acetonitrile affords white spars.

Workup

  1. custompartitioned between CH2Cl2 and aqueous NaHCO3
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-65100645ed5f426e93aa131ca3d0aed1
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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