Ethyl orthoformate → HCID 22479013, compound

HRID 1108644Notes

Reaction equation

HRID 1108644 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:25](OCC)(OCC)OCC>>[C:21]([O:20][C:18]([NH:17][CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[CH:25]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 18783942tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamate

Product 1

HCID 22479013HCID 22479013, compoundYield 88.5%

Procedure

21.37 g (64.67 mmol) of 3-amino-4-[4-(tert-butoxycarbonylamino)butylamino]quinoline was heated at 100° C. in 43.0 ml (258.7 mmol) of triethyl ortho-formate and stirred for 5 hours. The reaction mixture was concentrated to dryness, triturated with diethyl ether, and collected by filtration to obtain 19.49 g (57.25 mmol) of 1-[4-(tert-butoxycarbonylamino)butyl]-1H-imidazo[4,5-c]quinoline shown below as faint yellowish white powder.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with diethyl ether
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0008af4095ea4435bdfd8310133373a9
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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