2-(Methylamino)ethanol → HCID 22143489, compound

HRID 985226Notes

Reaction equation

HRID 985226 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O-:13])=O)[S:10][C:3]=12.[Li+].S(Cl)(Cl)=O.[CH3:19][NH:20][CH2:21][CH2:22][OH:23].CCN(CC)CC>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:20]([CH2:21][CH2:22][OH:23])[CH3:19])=[O:13])[S:10][C:3]=12

Participants

5

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 23677819Lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 22143489HCID 22143489, compoundYield 49.2%

Procedure

This material was prepared from lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate (1.0 g, 4.68 mmole) by treatment with thionyl chloride followed by reaction of the resultant acyl chloride with 2-(methylamino)ethanol (0.414 ml, 5.15 mmole) and Et3N (0.718 ml, 5.15 mmole), in a manner as previously described for example 9d to give a pale brown solid (0.624 g, 49% yield). 1H NMR (400 MHz, CDCl3) δ8.61 (1H, d, J=4.8 Hz), 7.80 (1H, s), 7.33 (1H, d, J=4.8 Hz), 3.92 (2H, m), 3.76 (2H, t, J=5.1 Hz), 3.37 (3H, s), 3.19 (1H, s); ESIMS (MH+): 259.10.

Sources & evidence

ORD record
ord-b5ab9bf07de8433380a103372f3595fe
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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