Isobutyryl chloride → HCID 58833642, compound

HRID 2203592Notes

Reaction equation

HRID 2203592 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-d62c9981a60848138ee6ce6f9255edc1
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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