1,1,1-Trimethoxybutane → HCID 57447006, compound

HRID 521293Notes

Reaction equation

HRID 521293 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][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:21](OC)(OC)(OC)[CH2:22][CH2:23][CH3:24]>>[CH2:22]([C:21]1[N:12]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[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)[CH2:23][CH3:24]

Participants

3

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 57447009HCID 57447009, compound

Product 1

HCID 57447006HCID 57447006, compoundYield 66.2%

Procedure

The general method described in Step 3 of Example 15 was used to cyclize ethyl 4-(3-aminoquinolin-4-ylamino)butyrate (18.0 g, 65.9 mmol) by reaction with trimethyl orthobutyrate (10.4 g, 70.2 mmol) to provide ethyl 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyrate (14.2 g) as a solid after chromatography on silica gel (elution with 5% methanol in dichloromethane).

Sources & evidence

ORD record
ord-971a0ea05cc8472aa61f681920b3624e
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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