HCID 67499458, compound → HCID 67499505, compound

HRID 2408195Notes

Reaction equation

HRID 2408195 reaction equation
[Cl:1][C:2]1[C:6]([NH:7][C:8](=[O:13])[CH2:9][CH2:10][S:11][CH3:12])=[CH:5][N:4]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[N:3]=1.[CH3:20][CH:21]([CH2:25][S:26][CH3:27])[C:22](Cl)=[O:23]>ClCCCl>[Cl:1][C:2]1[C:6]([N:7]([C:8](=[O:13])[CH2:9][CH2:10][S:11][CH3:12])[C:22](=[O:23])[CH:21]([CH3:20])[CH2:25][S:26][CH3:27])=[CH:5][N:4]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[N:3]=1

Participants

4

Reactant 2

HCID 67499458HCID 67499458, compoundHCID 758176512-Methyl-3-(methylthio)propanoyl chloride

Product 1

HCID 67499505HCID 67499505, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-(methylthio)propanamide (0.216 g, 0.728 mmol) in DCE (2.91 ml) in a 10 mL vial was added 2-methyl-3-(methylthio)propanoyl chloride (0.244 g, 1.601 mmol). The vial was capped and placed in a Biotage Initiator microwave reactor for 3 hours at 100° C., with external IR-sensor temperature monitoring from the side of the vessel. The crude mixture was concentrated and purified using reverse phase C-18 column chromatography (0-100% acetonitrile/water) to yield the title compound as a pale yellow oil (67 mg, 22%): IR (thin film) 2916 and 1714 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.96-8.92 (d, J=2.7 Hz, 1H), 8.64-8.59 (dd, J=4.9, 1.4 Hz, 1H), 8.07-7.99 (m, 2H), 7.50-7.40 (dd, J=8.4, 4.8 Hz, 1H), 3.39-3.28 (m, 1H), 3.10-2.99 (td, J=7.2, 3.9 Hz, 2H), 2.96-2.86 (dd, J=13.2, 8.7 Hz, 1H), 2.86-2.79 (t, J=7.3 Hz, 2H), 2.58-2.48 (dd, J=13.1, 5.8 Hz, 1H), 2.14-2.12 (s, 3H), 2.09-2.06 (s, 3H), 1.30-1.26 (d, J=6.9 Hz, 3H); ESIMS m/z 413 ([M+H]+).

Workup

  1. customThe vial was capped
  2. concentrationThe crude mixture was concentrated
  3. custompurified

Sources & evidence

ORD record
ord-127ab15117b640a4b5f03c56f4b42ed6
Source dataset
uspto-grants-2014_08
Patent number
US08815271B2

Reaction notes

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