1,1,1-Trimethoxybutane → HCID 57447034, compound

HRID 521312Notes

Reaction equation

HRID 521312 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][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:20](OC)(OC)(OC)[CH2:21][CH2:22][CH3:23]>>[CH2:21]([C:20]1[N:12]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[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)[CH2:22][CH3:23]

Participants

3

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 68874499HCID 68874499, compound

Product 1

HCID 57447034HCID 57447034, compoundYield 80.3%

Procedure

The general method described in Step 3 of Example 15 was used to cyclize ethyl 3-(3-aminoquinolin-4-ylamino)propionate (11.0 g, 42.4 mmol) by reaction with trimethyl orthobutyrate (7.22 g, 48.7 mmol) to provide ethyl 3-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propionate (10.6 g) as a dark oil that was used directly in the next step without further purification.

Sources & evidence

ORD record
ord-12ed1228d8c040239a0141b1708b9533
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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