1,1,1-Trimethoxybutane → HCID 57447053, compound

HRID 521289Notes

Reaction equation

HRID 521289 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][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:29](OC)(OC)(OC)[CH2:30][CH2:31][CH3:32]>>[CH2:30]([C:29]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[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)[CH2:31][CH3:32]

Participants

3

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 57447052HCID 57447052, compound

Product 1

HCID 57447053HCID 57447053, compoundYield 93.1%

Procedure

The general method described in Step 3 of Example 15 was used to cyclize ethyl 12-(3-aminoquinolin-4-ylamino)dodecanoate (30.4 g, 78.8 mmol) by reaction with trimethyl orthobutyrate (13.4 g, 90.6 mmol) to provide ethyl 12-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)dodecanoate (32.1 g) as a solid that was used directly in the next step without further purification.

Sources & evidence

ORD record
ord-e8b5a58cf3bd4114ae7a663c8f2c3bb2
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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