Reaction #2329064

Reaction equation

(2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1,3-thiazol-5-yl)acetic acid

(2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1.3-thiazol-5-yl)acetic acid

EDCI

triethylamine

morpholine

→

desired product

Yield 10.0%

3-chloro-2-methyl-N-[5-(2-morpholin-4-yl-2-oxoethyl)-1.3-thiazol-2-yl]benzenesulfonamide

Yield 10.0%

Solvents

CH2Cl2

DMF

Conditions

Workup

1. 1
   WashThe reaction mixture was then washed with 1 M HCl (2×15 mL)
2. 2
   Otherthe organic layer was collected
3. 3
   DryingThe organic phase was dried (MgSO4)
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherPurification

Procedure

To a solution of (2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1,3-thiazol-5-yl)acetic acid (Example 3) (0.09 g, 0.25 mmol) in CH2Cl2 (5.0 mL) and DMF (0.5 mL) were added EDCI (0.05 g, 0.27 mmol), DMAP (0.02 g, 0.12 mmol), triethylamine (0.1 mL, 0.75 mmol) and morpholine (0.03 mL, 0.30 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then washed with 1 M HCl (2×15 mL) and the organic layer was collected. The organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification using preparative HPLC afforded the desired product (0.01 g) in 10% yield.

Source