Imidazolate → Methyl 5-[2-(4-cyanophenyl)ethylcarbonylamino]-6-methylamino-nicotinate

HRID 50191

반응식

HRID 50191 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].[N-]1C=CN=C1.[NH2:19][C:20]1[C:21]([NH:30][CH3:31])=[N:22][CH:23]=[C:24]([CH:29]=1)[C:25]([O:27][CH3:28])=[O:26]>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([NH:19][C:20]2[C:21]([NH:30][CH3:31])=[N:22][CH:23]=[C:24]([CH:29]=2)[C:25]([O:27][CH3:28])=[O:26])=[O:13])=[CH:7][CH:8]=1)#[N:2]

참가 물질

5

반응물 3

HCID 3386966ImidazolateHCID 93617423-(4-Cyanophenyl)-propionic acidHCID 18412673Methyl 5-amino-6-(methylamino)pyridine-3-carboxylate

생성물 1

HCID 18412623Methyl 5-[2-(4-cyanophenyl)ethylcarbonylamino]-6-methylamino-nicotinate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2.6 g (15 mmol) of 3-(4-cyanophenyl)propionic acid in 25 mL of absolute tetrahydrofuran was mixed with 2.4 g (15 mmol) of N,N′-carbonyldiimidazole and stirred for 20 minutes at room temperature. Then the imidazolide was mixed with a solution of 2.3 g (13 mmol) of methyl 5-amino-6-methylaminonicotinate in 25 mL of dimethyfformamide and heated for 3 hours to 100° C. After the removal of the solvent in vacuo, the crude product obtained was taken up in ethyl acetate, the organic phase was washed with water and after drying over sodium sulfate it was again freed from solvent. The residue obtained was purified by flash chromatography (silica gel; gradient: dichloromethane to dichloromethane/ethanol=19:1). Yield: 2.1 g (50% of theory) of beige solid; Rf value: 0.54 (silica gel; ethyl acetate/ethanol/ammonia=90:10:1).

후처리

  1. temperatureheated for 3 hours to 100° C
  2. customAfter the removal of the solvent in vacuo

출처 및 근거

ORD 기록
ord-8ed547a2fc2a4ce58ab475f72df20328
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710055B2

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