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

HRID 23639

Reaction equation

[CH2:1]([O:4][CH2:5][C:6]1[C:10]2[N:11]([CH3:27])[CH:12]=[C:13]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[O:17])[C:14](=[O:15])[C:9]=2[S:8][CH:7]=1)[CH:2]=[CH2:3].[Li+].CC([N-]C(C)C)C.C(NC(C)C)(C)C.Cl.C1C[O:47][CH2:46]C1>C(Cl)Cl.C(Cl)(Cl)Cl.CN(C=O)C>[CH2:1]([O:4][CH2:5][C:6]1[C:10]2[N:11]([CH3:27])[CH:12]=[C:13]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[O:17])[C:14](=[O:15])[C:9]=2[S:8][C:7]=1[CH:46]=[O:47])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a cold (−78° C.), stirred solution of 922 mg of 3-[(allyloxy)methyl]-N-(4-chlorobenzyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 30 mL of dry THF, under argon, is added via cannula a THF solution of LDA, prepared in the usual manner from 1.3 mL of diisopropylamine and 2.7 mL of 2.5 M (hexanes) butyllithium in 20 mL of THF. The solution is stirred at −78° C. for 10 min, then 0.89 mL of dry DMF is added, and the mixture is allowed to warm to 0° C. After 10 min, aqueous workup (CHCl3/dil. HCl) is performed and is followed by flash chromatography on silica using 1.5% MeOH in CH2Cl2 to provide 620 mg of the title compound as a yellow-orange solid. Recrystallization from EtOAc gives yellow crystals.

Workup

temperatureto warm to 0° C
waitAfter 10 min

Sources & evidence

ORD record: ord-f9cd6a124c0544f4a02dcb2296421b38
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852731B2

Linked notes

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