Sodium Bicarbonate → N-(4-Chlorobenzyl)-3-(hydroxymethyl)-2-{[(2-hydroxy-2-quinolin-2-ylethyl)(methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23649Notes

Reaction equation

HRID 23649 reaction equation
[Cl:1][C:2]1[CH:46]=[CH:45][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:44])[C:12]3[S:19][C:18]([CH2:20][N:21]([CH2:23][CH:24]([OH:35])[C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]=4)[CH3:22])=[C:17]([CH2:36][O:37]CC[Si](C)(C)C)[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)(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:44])[C:12]3[S:19][C:18]([CH2:20][N:21]([CH2:23][CH:24]([OH:35])[C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]=4)[CH3:22])=[C:17]([CH2:36][OH:37])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:45][CH:46]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 22574370HCID 22574370, compound

Product 1

HCID 22574421N-(4-Chlorobenzyl)-3-(hydroxymethyl)-2-{[(2-hydroxy-2-quinolin-2-ylethyl)(methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 98.5%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 174 mg of N-(4-chlorobenzyl)-2-{[(2-hydroxy-2-quinolin-2-ylethyl)(methyl)amino]methyl}-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 2.5 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 3% MeOH in CH2Cl2 provides 146 mg of the title compound as a white solid. Recrystallization from EtOAc-hexane affords white solid.

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-6a70f7699a5c4ca686680dc8e075f61a
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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