Dimethylamine → 7-Chloro-N,N-dimethylthieno[3,2-b]pyridine-2-carboxamide

HRID 1825106Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([OH:13])=O)[S:10][C:3]=12.O=S(Cl)Cl.[CH3:18][NH:19][CH3:20].C1COCC1.CCN(CC)CC>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:19]([CH3:20])[CH3:18])=[O:13])[S:10][C:3]=12

Participants

Reactant 5

HCID 674Dimethylamine

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 24386Thionyl Chloride

HCID 112760337-Chlorothieno[3,2-b]pyridine-2-carboxylic acid

Product 1

HCID 221435377-Chloro-N,N-dimethylthieno[3,2-b]pyridine-2-carboxamideYield 84%

Procedure

This material was prepared from 7-chlorothieno[3,2-b]pyridine-2-carboxylic acid (0.57 g, 2.67 mmole), SOCl2 (5 ml), 2.0 M N,N-dimethylamine in THF (1.60 ml, 3.20 mmole) and Et3N (0.447 ml, 3.20 mmole) in a manner as previously described for example 9d to give a brown solid (0.54 g, 84%). 1H NMR (300 MHz, CDCl3) δδδ 1H, d, J=5.0 Hz), 7.74 (1H, s), 7.35 (1H, d, J=5.0 Hz), 3.28 (3H, s), 3.22 (3H, s); ESIMS (MH+): 240.95.

Sources & evidence

ORD record: ord-bbc8dc960ed34af499ce4e82d093288a
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

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