Azetidine → 2-(Azetidin-1-ylcarbonyl)-7-chlorothieno[3,2-b]pyridine

HRID 985217Notes

Reaction equation

HRID 985217 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.[NH:19]1[CH2:22][CH2:21][CH2:20]1>>[N:19]1([C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:8]=2)=[O:13])[CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 3

HCID 10422AzetidineHCID 24386Thionyl ChlorideHCID 23677819Lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 221435492-(Azetidin-1-ylcarbonyl)-7-chlorothieno[3,2-b]pyridineYield 83%

Procedure

This material was prepared from lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate (100 mg, 0.47 mmole) by treatment with thionyl chloride followed by coupling with azetidine, in a manner as previously described for example 9d to afford 98 mg (83%) of a dark yellow solid. 1H NMR (DMSO-d6) δ8.72 (1H, d, J=5.1 Hz), 7.96 (1H, s), 7.70 (1H, d, J=5.1 Hz), 4.62 (2H, t, J=7.4 Hz), 4.12 (2H, t, J=7.7 Hz), 2.34 (2H, tt, J=7.4, 7.7 Hz). Anal. Calcd for C11H9N2OSCl: C, 52.28; H, 3.59; Cl, 14.03; N, 11.09; S, 12.69. Found: C, 52.39; H, 3.63; Cl, 14.29; N, 10.99; S, 12.74.

Sources & evidence

ORD record
ord-1e02cf67e1c3412cafff2ae0e39166dd
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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