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

HRID 23652Notes

Reaction equation

HRID 23652 reaction equation
[N:1]([CH2:4][C:5]1[C:9]2[N:10]([CH3:26])[CH:11]=[C:12]([C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[O:16])[C:13](=[O:14])[C:8]=2[S:7][C:6]=1[CH:27]=[O:28])=[N+:2]=[N-:3].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[N:1]([CH2:4][C:5]1[C:9]2[N:10]([CH3:26])[CH:11]=[C:12]([C:15]([NH:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)=[O:16])[C:13](=[O:14])[C:8]=2[S:7][C:6]=1[CH2:27][OH:28])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 225744043-(Azidomethyl)-N-(4-chlorobenzyl)-2-formyl-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 225744093-(Azidomethyl)-N-(4-chlorobenzyl)-2-(hydroxymethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 64.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.), stirred solution of 230 mg of 3-(azidomethyl)-N-(4-chlorobenzyl)-2-formyl-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 6 mL of CH2Cl2 is added 0.16 mL of acetic acid and 296 mg of sodium triacetoxyborohydride. The ice bath is removed and the solution allowed to stir at room temperature for 2 h. Aqueous workup (CHCl3/aq. NaHCO3) followed by flash chromatography on silica using 3% MeOH in CH2Cl2 affords 150 mg of the title compound as a white solid. Recrystallization from acetonitrile provides off-white crystals.

Workup

  1. customThe ice bath is removed

Sources & evidence

ORD record
ord-edcd8a6fa5404c83bd40d7a7f949ffc8
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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