Ethyl orthoformate → HCID 12016825, compound

HRID 1837010Notes

Reaction equation

HRID 1837010 reaction equation
[CH:1](OCC)(OCC)OCC.[NH2:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:21]=1[NH:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:19][CH:18]=[CH:17][CH:16]=2>C1(C)C=CC=CC=1>[N:22]1([CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[CH:1]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 12016824tert-Butyl 2-(3-aminoquinolin-4-ylamino)ethylcarbamate

Product 1

HCID 12016825HCID 12016825, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethyl orthoformate (11.3 g, 73.4 mmol) was added to a solution of tert-butyl N-[2-(3-aminoquinolin-4-yl)aminoethyl]carbamate (21 g, 69.4 mmol) in anhydrous toluene (250 mL). The reaction mixture was heated at reflux for 5 hours and then allowed to slowly cool to ambient temperature. The resulting precipitate was isolated by filtration and dried to provide 17.6 g of tert-butyl N-[2-(1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate as a light tan solid, m.p. 154-155° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 hours
  3. customThe resulting precipitate was isolated by filtration
  4. customdried

Sources & evidence

ORD record
ord-9c65ff30eb9740598eb57fca828fca7d
Source dataset
uspto-grants-2004_08
Patent number
US06780873B2

Reaction notes

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