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

HRID 735467Notes

Reaction equation

HRID 735467 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b1a82ac105a645bba8335657b8f644e0
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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