Isobutylamine → HCID 178494565, compound

HRID 365346Notes

Reaction equation

HRID 365346 reaction equation
[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([NH2:23])=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2].[CH2:24]([NH2:28])[CH:25]([CH3:27])[CH3:26]>COCCOC.[O-2].[O-2].[Mn+4]>[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[C:16]1[NH:28][C:24]([CH:25]([CH3:27])[CH3:26])=[N:23][C:15]1=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6558IsobutylamineHCID 54330911HCID 54330911, compound

Product 1

HCID 178494565HCID 178494565, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

627 mg of 6-amino-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester is stirred in 10 ml of ethylene glycol dimethyl ether with 1.6 g of manganese dioxide and 0.98 ml of isobutylamine for 16 hours at room temperature. The reaction mixture is filtered on Celite, the filtrate is concentrated by evaporation and chromatographed on silica gel with methylene chloride and ethanol=10+1. 499 mg of 2-isopropyl-10-methoxymethyl-1H-imidazo[4,5-g]-β-carboline-9-carboxylic acid isopropyl ester (oily) is obtained from the desired fractions.

Workup

  1. filtrationThe reaction mixture is filtered on Celite
  2. concentrationthe filtrate is concentrated by evaporation
  3. customchromatographed on silica gel with methylene chloride and ethanol=10+1

Sources & evidence

ORD record
ord-e0c1036442844ab1835eab32fd309028
Source dataset
uspto-grants-2000_10
Patent number
US06127368

Reaction notes

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