反応 #166772

反応方程式

4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-amine

(S)—N-(4-(4-(2-(4-chlorophenyl)-3-(isopropylamino)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)butyramide

Na2CO3

triethylamine

Triethylamine

nicotinic acid

→

N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide

収率 59.6%

溶媒

DMF

MeOH

LiOH

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirred for 10 minutes
3. 3
   抽出extracted into DCM
4. 4
   その他dried
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他to give a crude residue that
8. 8
   その他was purified by column chromatography (500:20-500:30 DCM:MeOH)

実験手順

Crude 4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-amine (0.200 g, 0.651 mmol, see Example 25), nicotinic acid (0.0961 g, 0.781 mmol) and triethylamine (0.453 mL, 3.25 mmol) were placed in DMF (3 mL) at room temperature. Triethylamine (0.453 mL, 3.25 mmol) was then added, and the reaction was stirred for 1 hour at room temperature. The reaction was then diluted with MeOH (5 mL), and 3M LiOH (0.5 mL) was added and stirred for 10 minutes. The reaction was then poured into saturated Na2CO3 and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated to give a crude residue that was purified by column chromatography (500:20-500:30 DCM:MeOH) to give N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.160 g, 59.6% yield).

出典