Isobutyryl chloride → HCID 23512736, compound

HRID 353906Notes

Reaction equation

HRID 353906 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[C:6]1[CH3:19].[C:20](Cl)(=[O:24])[CH:21]([CH3:23])[CH3:22]>>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH3:19])[N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

3

Reactant 2

HCID 62325Isobutyryl chlorideHCID 22344446HCID 22344446, compound

Product 1

HCID 23512736HCID 23512736, compoundYield 43.6%

Procedure

Using the general method of Example 205, 1-(3-aminopropyl)-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 7.83 mmol) was reacted with isobutyryl chloride (835 mg, 7.83 mmol). The product was recrystallized from methyl acetate to provide 1.11 g of N-[3-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-2-methylpropanamide as an off white powder, m.p. 239.0-240.1° C. Analysis: Calculated for C18H23N5O.0.20 C3H6O2: % C, 65.66; % H, 7.17; % N, 20.58. Found: % C, 65.51. % H, 7.05; % N, 20.71.

Workup

  1. customThe product was recrystallized from methyl acetate

Sources & evidence

ORD record
ord-a65a0ec0c7ee4702b60e552e8908e655
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Reaction notes

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