Trimethyl orthoformate → HCID 68928912, compound

HRID 521322Notes

Reaction equation

HRID 521322 reaction equation
[CH3:1][C:2]([CH3:23])([CH2:16][C:17]1([CH3:22])[O:21][CH2:20][CH2:19][O:18]1)[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15].[CH:24](OC)(OC)OC>>[CH3:1][C:2]([CH3:23])([CH2:16][C:17]1([CH3:22])[O:21][CH2:20][CH2:19][O:18]1)[CH2:3][N:4]1[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=[CH:24]1

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 86611638HCID 86611638, compound

Product 1

HCID 68928912HCID 68928912, compoundYield 270.4%

Procedure

The general method described in Step 6 of Example 22 was used to cyclize N4-[2,2-dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)propyl]quinoline-3,4-diamine (8.1 g, 25.7 mmol) by reaction with trimethyl orthoformate (3.3 g, 10 mmol) to provide 1-[2,2-dimethyl-3-(2-methyl[1,3]dioxolan-2-yl)propyl]-1H-imidazo[4,5-c]quinoline (8.8 g) as an oil that was used directly in the next step without further purification.

Sources & evidence

ORD record
ord-e587b4552dc74fca914581bef3ccf73f
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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