Methanamine, N-methoxy-, hydrochloride (1:1) → 2-Benzyl-3-phenyl-2h-indazole-7-carboxylic acid methoxy-methyl-amide

HRID 735467노트

반응식

HRID 735467 반응식
[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:23](O)=[O:24])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:39][NH:40][O:41][CH3:42]>N1C=CC=CC=1>[CH3:42][O:41][N:40]([CH3:39])[C:23]([C:11]1[C:10]2[C:15](=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:9]=2)[CH:14]=[CH:13][CH:12]=1)=[O:24]

참가 물질

5

반응물 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67021115HCID 67021115, 화합물

생성물 1

HCID 872393912-Benzyl-3-phenyl-2h-indazole-7-carboxylic acid methoxy-methyl-amide

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

2-Benzyl-3-phenyl-7-trifluoromethyl-2H-indazole (353 mg, 1 mmol), prepared similarly to that of Example 1, was treated with 3 ml of 70% aq H2SO4 at 90° C. for 4 hours. After cooling, 10 volumes of water were added and the product was extracted with dichloromethane. Flash column chromatography (SiO2, dichloromethane as an eluant) afforded 2-benzyl-3-phenyl-2H-indazole-7-carboxylic acid in 60% yleld. The 2-benzyl-3-phenyl-2H-indazole-7-carboxylic acid (1.64 g, 5 mmol) was dissolved in 20 ml of pyridine followed by addition of 1-(-3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.34 g, 7 mmol) and N,O-dimethyhydroxylamine hydrochloride (585 mg, 6 mmol). The reaction mixture was stirred at room temperature overnight. Pyridine was evaporated and the residue was shaken with 0.5M aq HCl and dichloromethane. The product was extracted with dichloromethane, and flash column chromatography (SiO2, dichloromethane as an eluant) afforded 2-benzyl-3-phenyl-2H-indazole-7-carboxylic acid methoxy-methyl-amide in 79% yleld.

후처리

  1. customPyridine was evaporated
  2. stirringthe residue was shaken with 0.5M aq HCl and dichloromethane
  3. extractionThe product was extracted with dichloromethane, and flash column chromatography (SiO2, dichloromethane as an eluant)

출처 및 근거

ORD 기록
ord-b1a82ac105a645bba8335657b8f644e0
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592363B2

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