Isobutyryl chloride → HCID 58833642, compound

HRID 540917Notes

Reaction equation

HRID 540917 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:26][CH2:27][CH3:28])[C:7]2[C:16]3[CH:15]=[C:14]([O:17][CH:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)[CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:24])[C:8]=2[N:25]=1)[CH3:2].[C:29](Cl)(=[O:33])[CH:30]([CH3:32])[CH3:31]>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:26][CH2:27][CH3:28])[C:7]2[C:16]3[CH:15]=[C:14]([O:17][CH:18]4[CH2:19][CH2:20][N:21]([C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[CH2:22][CH2:23]4)[CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:24])[C:8]=2[N:25]=1)[CH3:2]

Participants

3

Reactant 2

HCID 62325Isobutyryl chlorideHCID 58833720HCID 58833720, compound

Product 1

HCID 58833642HCID 58833642, compound

Procedure

A modification of the procedure described in Example 413 was used. 2-(Ethoxymethyl)-8-(piperidin-4-yloxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 411, 0.650 g, 1.69 mmol) was treated with isobutyryl chloride instead of the methanesulfonic anhydride. After the work up, the crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 2-25% CMA in chloroform) followed by recrystallization from acetonitrile to yield 0.500 g of 2-(ethoxymethyl)-8-[(1-isobutyrylpiperidin-4-yl)oxy]-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 177-179° C.

Workup

  1. customAfter the work up, the crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 2-25% CMA in chloroform)
  2. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-bd598d0949664ecb8563d50f62a09b0c
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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