Ethyl orthoformate → HCID 22479013, compound

HRID 1368119Notes

Reaction equation

HRID 1368119 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:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:25](OCC)(OCC)OCC>>[N:12]1([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[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

Participants

3

Reactant 2

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

Product 1

HCID 22479013HCID 22479013, compound

Procedure

Using the general method of Example 1 Part C, tert-butyl N-(4-[(3-aminoquinolin-4-yl)amino]butyl)carbamate (149 g, 0.451 mol) was reacted with triethyl orthoformate to provide crude product. This material was recrystallized from isopropyl alcohol to provide 84 g of tert-butyl N-[4-(1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate as a crystalline solid.

Workup

  1. customto provide crude product
  2. customThis material was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-024d041c98b64b89afa773b068ee73c6
Source dataset
uspto-grants-2003_06
Patent number
US06573273B1

Reaction notes

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