Ethyl orthoformate → 1-[3-(tert-butoxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline

HRID 1108630Notes

Reaction equation

HRID 1108630 reaction equation
[CH:1](OCC)(OCC)OCC.[NH2:11][C:12]1[C:13]([Cl:34])=[N:14][C:15]2[C:20]([C:21]=1[NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:19][CH:18]=[CH:17][CH:16]=2>>[C:30]([O:29][C:27]([NH:26][CH2:25][CH2:24][CH2:23][N:22]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([Cl:34])[C:12]=2[N:11]=[CH:1]1)=[O:28])([CH3:31])([CH3:33])[CH3:32]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 187839403-Amino-4-[3-(tert-butoxycarbonylamino)propylamino]-2-chloro-quinoline

Product 1

HCID 187839501-[3-(tert-butoxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinolineYield 90.7%

Conditions

Temperature
100 °C

Procedure

0.36 ml (2.14 mmol) of triethyl ortho-formate was added to 0.15 g (0.428 mmol) of 3-amino-4-[3-(tert-butoxycarbonylamino)-propylamino]-2-chloro-quinoline. The mixture was stirred at 100° C. for 2 hours and then at 80° C. for overnight. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol 150:1 to 100:1 (v/v)) to obtain 0.14 g (0.388 mmol) of 1-[3-(tert-butoxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline shown below as white powder (mp: 155-156° C.). ##STR36## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3380, 1680, 1520.

Workup

  1. waitat 80° C. for overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (chloroform:methanol 150:1 to 100:1 (v/v))

Sources & evidence

ORD record
ord-2cf25c6bf2d040c19d3accd7f7e691f2
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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