Sodium Bicarbonate → 2-{[[2-(1-Benzofuran-2-yl)-2-hydroxyethyl](methyl)amino]methyl}-N-(4-chlorobenzyl)-3-(hydroxymethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23647Notes

Reaction equation

HRID 23647 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]([OH:45])[CH2:11][N:12]([CH2:14][C:15]1[S:23][C:22]2[C:21](=[O:24])[C:20]([C:25]([NH:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)=[O:26])=[CH:19][N:18]([CH3:36])[C:17]=2[C:16]=1[CH2:37][O:38]CC[Si](C)(C)C)[CH3:13].C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]([OH:45])[CH2:11][N:12]([CH2:14][C:15]1[S:23][C:22]2[C:21](=[O:24])[C:20]([C:25]([NH:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)=[O:26])=[CH:19][N:18]([CH3:36])[C:17]=2[C:16]=1[CH2:37][OH:38])[CH3:13]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 225743282-{[[2-(1-benzofuran-2-yl)-2-hydroxyethyl](methyl)amino]methyl}-N-(4-chlorobenzyl)-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 225744082-{[[2-(1-Benzofuran-2-yl)-2-hydroxyethyl](methyl)amino]methyl}-N-(4-chlorobenzyl)-3-(hydroxymethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 78.7%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 154 mg of 2-{[[2-(1-benzofuran-2-yl)-2-hydroxyethyl](methyl)amino]methyl}-N-(4-chlorobenzyl)-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 3 mL of 75% TFA in CH2Cl2 is stirred at room temperature for 4 h, then diluted with CHCl3 and added to stirred aq. NaHCO3. The aqueous phase is extracted with 4 portions of CH2Cl2, and the combined organic phases dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica gel using 4% MeOH in CH2Cl2 provides 103 mg of the title compound as a pale yellow solid. Recrystallization from acetonitrile affords white needles.

Workup

  1. additionadded
  2. extractionThe aqueous phase is extracted with 4 portions of CH2Cl2
  3. dry with materialthe combined organic phases dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89fbb84a9e0d4acea2bc7a58057f2492
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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