1,1,1-Trimethoxybutane → ethyl 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoate

HRID 2366681Notes

Reaction equation

HRID 2366681 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][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:22](OC)(OC)(OC)[CH2:23][CH2:24][CH3:25]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:23]([C:22]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[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]=1)[CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 57447068Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate

Product 1

HCID 57447069ethyl 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoateYield 90.2%

Reagents, catalysts & solvents 1

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)Catalyst

Procedure

The method described in Part A of Example 10 was used to treat ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate (26.3 g, 91.5 mmol) with trimethyl orthobutyrate (18.3 mL, 114 mmol) and pyridinium p-toluenesulfonate (0.5 g). The reaction was complete in three hours to provide 28 g of ethyl 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoate as a brown oil.

Sources & evidence

ORD record
ord-d265c4f0bb934649b9d08aadc4bcb426
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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