2-Pentanone, 5-chloro- → HCID 67187114, compound

HRID 885956Notes

Reaction equation

HRID 885956 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[S:5][C:6]=1[C:7]([NH2:9])=[O:8].Cl[CH2:17][CH2:18][CH2:19][C:20](=O)[CH3:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCCl>[CH3:17][C:18]12[CH2:19][CH2:20][CH2:21][N:1]1[C:2]1[N:3]=[C:4]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:5][C:6]=1[C:7](=[O:8])[NH:9]2

Participants

5

Reactant 3

HCID 799932-Pentanone, 5-chloro-HCID 521998p-Toluenesulfonic acid monohydrateHCID 13595332HCID 13595332, compound

Product 1

HCID 67187114HCID 67187114, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A stirred solution of 4-amino-2-(morpholin-4-yl)-1,3-thiazole-5-carboxamide (0.22 g, 0.99 mmol), 5-chloro-2-pentanone (0.5 mL, excess) and p-toluenesulfonic acid monohydrate (cat. amount) in DCE (4 mL) was heated to 100° C. in a sealed tube, under microwave irradiation, for 1 h. The reaction mixture was then concentrated in vacuo and purification by preparative HPLC gave the title compound (0.03 g, 10%) as an off-white solid. δH (DMSO-d6) 7.29 (1H, s), 3.73-3.64 (4H, m), 3.57-3.39 (6H, m), 2.08-1.96 (2H, m), 1.93-1.83 (2H, m), 1.36 (3H, s). LCMS (ES+) 295.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo and purification by preparative HPLC

Sources & evidence

ORD record
ord-a382a43cfa464c8b988fd49ec485392d
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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