6-(Cyclopropylmethoxy)-5-(3-methoxyazetidin-1-yl)picolinic acid → 3-[6-(Cyclopropylmethoxy)-5-(3-methoxyazetidin-1-yl)pyridine-2-carbonyl]-1,1-dioxo-1,3-thiazolidine-4-carboxamide

HRID 624989Notes

Reaction equation

HRID 624989 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][C:7]=2[N:15]2[CH2:18][CH:17]([O:19][CH3:20])[CH2:16]2)[CH2:3][CH2:2]1.Cl.[O:22]=[S:23]1(=[O:31])[CH2:27][CH:26]([C:28]([NH2:30])=[O:29])[NH:25][CH2:24]1>>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([N:25]3[CH:26]([C:28]([NH2:30])=[O:29])[CH2:27][S:23](=[O:31])(=[O:22])[CH2:24]3)=[O:14])[CH:9]=[CH:8][C:7]=2[N:15]2[CH2:18][CH:17]([O:19][CH3:20])[CH2:16]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 902034536-(Cyclopropylmethoxy)-5-(3-methoxyazetidin-1-yl)picolinic acidHCID 902038431,1-Dioxo-1,3-thiazolidine-4-carboxamide hydrochloride

Product 1

HCID 902035683-[6-(Cyclopropylmethoxy)-5-(3-methoxyazetidin-1-yl)pyridine-2-carbonyl]-1,1-dioxo-1,3-thiazolidine-4-carboxamideYield 33%

Procedure

In analogy to the procedure described in Example 127 e), 6-(cyclopropylmethoxy)-5-(3-methoxyazetidin-1-yl)pyridine-2-carboxylic acid (Example 128 a, 30 mg, 108 μmol) was reacted with 1,1-dioxo-1,3-thiazolidine-4-carboxamide hydrochloride (Example 127 d, 26.0 mg, 129 μmol) to give the title compound (15 mg, 33%) as off-white solid, MS (EI): m/e=425.5 [MH+].

Sources & evidence

ORD record
ord-27f172082ca247ac89f97b2f5e1536df
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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