تفاعل #1857596

معادلة التفاعل

1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-amine hydrochloride

3-methoxybenzoic acid

EDC

triethyl amine

→

N-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-3-methoxybenzamide

المردود 43.6%

المذيبات

DCM

DCM

ظروف التفاعل

المعالجة

1. 1
   غسيلthe organic phase was washed with aqueous 0.1 N HCL (150 mL)
2. 2
   تجفيفThe organic layer was dried over sodium sulfate
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated on the rotovap
5. 5
   أخرىThe crude product was purified by silica gel chromotography (40% ethyl acetate in hexanes)
6. 6
   أخرىto afford 225 mg of an off white solid
7. 7
   أخرىThe solid was triturated with ethyl acetate/hexanes (1/9)
8. 8
   ترشيحthe white solid was collect by filtration
9. 9
   workup.DISSOLUTIONThe pure product was dissolved in absolute ethanol
10. 10
    تركيزconcentrated on the rotovap (4×, 25 mL)

الإجراء التجريبي

1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-amine hydrochloride (Example 4-1a) (300 mg, 1.3 mmol), 3-methoxybenzoic acid (172 mg, 1.3 mmol), EDC (386 mg, 2 mmol), and triethyl amine (303 mg, 3 mmol) were stirred in DCM (5 mL) at ambient temperature for 6 hours. The reaction was diluted with DCM (50 mL) and the organic phase was washed with aqueous 0.1 N HCL (150 mL) followed by aqueous 1N NaOH (150 mL). The organic layer was dried over sodium sulfate, filtered and concentrated on the rotovap. The crude product was purified by silica gel chromotography (40% ethyl acetate in hexanes) to afford 225 mg of an off white solid. The solid was triturated with ethyl acetate/hexanes (1/9) and the white solid was collect by filtration. The pure product was dissolved in absolute ethanol and concentrated on the rotovap (4×, 25 mL) to afford N-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-3-methoxybenzamide (185 mg, 43%) as a white solid. NMR (CDCl3, 400 MHz): b 2.20 (s, 3H), 2.42 (s, 3H), 3.85 (s, 3H), 5.03 (s, 2H), 7.09-7.06 (m, 1H), 7.37-7.35 (m, 2H), 7.41 (m, 1H), 7.51 (s, 1H), 7.93 (bs, 1H), 8.03 (s, 1H). LC/MS; [M+H] calculated for C17H18N4O3; expected 327.14. Found 327.30. Melting point: 127-129° C.

المصدر