Methanesulfonyl chloride → HCID 10178699, compound

HRID 2296951Notes

Reaction equation

HRID 2296951 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])=[CH:4][CH:3]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[CH:18]1([CH2:17][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:7][CH:6]=2)[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 99488022-(4-amino-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide

Product 1

HCID 10178699HCID 10178699, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(4-amino-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (prepared in Example 3, 158 mg, 0.5 mmol) in pyridine (5 mL) at 25° C. was treated with methanesulfonyl chloride (50 μL, 0.57 mmol ). The reaction was stirred at 25° C. for 7 h and was then concentrated in vacuo. High pressure liquid chromatography (Chromegasphere SI-60, 10 μM, 60 Å, 25 cm×23 cm ID, 40/60 heptane/ethyl acetate) afforded 3-cyclopentyl-2-(4-methanesulfonylamino-phenyl)-N-thiazol-2-yl-propionamide (98.2 mg, 49.9%) as a tan solid: mp 85-90° C.; EI-HRMS m/e calcd for C18H23N3O3S (M+) 393.1180, found 393.1185.

Workup

  1. concentrationwas then concentrated in vacuo

Sources & evidence

ORD record
ord-2698af81d9664a2abb556fa3efb019cb
Source dataset
uspto-grants-2002_12
Patent number
US06489485B2

Reaction notes

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