反応 #1004960

反応方程式

product

4-(3,4-Dichloro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

ammonia

PyBOP

→

4-(3,4-Dichloro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid amide

収率 12.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他The reaction mixture was quenched with acetic acid (ca. 0.5 mL)
2. 2
   workup.ADDITIONdiluted with ethyl acetate (40 mL)
3. 3
   洗浄washed with water (2×10 mL) and saturated brine (10 mL)
4. 4
   乾燥The organics were dried over magnesium sulfate
5. 5
   濃縮concentrated in vacuo
6. 6
   その他chromatographed on silica gel
7. 7
   洗浄Elution with dichloromethane-methanol (4:1)

実験手順

The product of step A (234 mg) was dissolved in dichloromethane (5 mL) and ethanolic ammonia (2 M, 2.0 mL, 4.0 mmol): PyBOP (579 mg, 1.10 mmol) was added in one portion and the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was quenched with acetic acid (ca. 0.5 mL), diluted with ethyl acetate (40 mL) and washed with water (2×10 mL) and saturated brine (10 mL). The organics were dried over magnesium sulfate, concentrated in vacuo and chromatographed on silica gel. Elution with dichloromethane-methanol (4:1) afforded 4-(3,4-Dichloro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid amide (28 mg, 12% yield) as a dark yellow-colored solid. An analytical sample was prepared by crystallization from methanol: m.p. >250° C.; 1H NMR (DMSO-d6, 400 MHz) δ10.38 (s, 1H), 8.30 (s, 1H), 7.85 (br s, 1H), 7.57 (d, J=8.8 Hz, 1H), 7.48 (d, J=2.4 Hz, 1H), 7.45 (br s, 1H), 7.23 (dd, J=8.8, 2.4 Hz, 1H), 5.70 (s, 1H), 3.33 (s, 3H). Anal. Calcd./Found for C13H11Cl2N3O2: C, 50.02/50.02; H, 3.55/3.19; N, 13.46/13.21.

出典