Cesium carbonate → Tert-butyl[2-(4-amino-2-ethoxymethyl-1-propyl-1h-imidazo[4,5-c]quinolin-7-yloxy)ethyl]carbamate

HRID 540864Notes

Reaction equation

HRID 540864 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:18][O:19][CH2:20][CH3:21])[N:14]([CH2:15][CH2:16][CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:22])=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36]>>[C:35]([O:34][C:33](=[O:39])[NH:32][CH2:31][CH2:30][O:22][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:14]([CH2:15][CH2:16][CH3:17])[C:13]([CH2:18][O:19][CH2:20][CH3:21])=[N:12][C:11]=3[C:2]([NH2:1])=[N:3][C:4]=2[CH:5]=1)([CH3:38])([CH3:37])[CH3:36]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 641024tert-butyl N-(2-iodoethyl)carbamateHCID 1360752014-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-7-ol

Product 1

HCID 131731978Tert-butyl[2-(4-amino-2-ethoxymethyl-1-propyl-1h-imidazo[4,5-c]quinolin-7-yloxy)ethyl]carbamateYield 45.2%

Procedure

The method described in Part L of Example 2 was used to treat 4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-7-ol (1.89 g, 6.29 mmol) with cesium carbonate (4.10 g, 12.6 mmol) and tert-butyl 2-iodoethylcarbamate (1.79 g, 6.60 mmol). Following chromatographic purification, the product was recrystallized from acetonitrile to provide 1.26 g of tert-butyl[2-(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-7-yloxy)ethyl]carbamate as a flocculent, white solid.

Workup

  1. custompurification
  2. customthe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-83057e5c4cec4ef68f3380e51622fe98
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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