Piperidine → 5-Methyl-6-(piperidine-1-sulfonyl)-pyridine-2-carboxylic acid methyl ester

HRID 632000Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([S:12]([OH:15])(=[O:14])=O)[N:6]=1)=[O:4].S(Cl)(Cl)=O.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([S:12]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)(=[O:14])=[O:15])[N:6]=1)=[O:4]

Participants

Conditions

Temperature: 40 °C

Procedure

5-Methyl-6-sulfo-pyridine-2-carboxylic acid methyl ester (340 mg, 1.47 mmol), thionyl chloride (CAN 7719-09-7, 1 mL) and 1 drop of DMF were added to methylene chloride (10 mL), and the mixture was stirred for 2 h at 40° C. The mixture was cooled to room temperature, and piperidine (CAN 110-89-4, 1.0 g, 12 mmol) in methylene chloride (10 mL) was added to the above mixture. The solvent was removed in vacuo, and the crude product was purified by prep-HPLC (eluting with 50% ethyl acetate in petroleum ether) to give the product (53 mg, 12%); MS (EI): m/e=299.1 [M+H]+.

Workup

temperatureThe mixture was cooled to room temperature
customThe solvent was removed in vacuo
customthe crude product was purified by prep-HPLC (eluting with 50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-04768e86b0bd4072a98f2f4f99d9b4ea
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321727B2

Reaction notes

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