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

HRID 23651Notes

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][CH:6]=1)=[N+:2]=[N-:3].[Li+].CC([N-]C(C)C)C.C(NC(C)C)(C)C.Cl.C1C[O:46][CH2:45]C1>C(Cl)Cl.C(Cl)(Cl)Cl.CN(C=O)C>[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[CH:45]=[O:46])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: -78 °C

Procedure

Into a cold (−78° C.), stirred mixture of 2.54 g of 3-(azidomethyl)-N-(4-chlorobenzyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 100 mL of dry THF is added via cannula a solution of LDA in THF, prepared from 3.7 mL of diisopropylamine and 8.0 mL of 2.5 M (hexanes) butyllithium in 50 mL of THF. The mixture is stirred at −78° C. for 90 min, then 2.5 mL of dry DMF is added and the mixture is allowed to warm to 0° C. Aqueous workup (CHCl3/dil. HCl) followed by flash chromatography on silica using 2% MeOH in CH2Cl2 affords 1.61 g of the title compound as an amber foam.

Workup

stirringThe mixture is stirred at −78° C. for 90 min
temperatureto warm to 0° C

Sources & evidence

ORD record: ord-715d8e8dd267402f926aa0755caa9e40
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852731B2

Reaction notes

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