Water → HCID 58833664, compound

HRID 540912Notes

Reaction equation

HRID 540912 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[CH:30][C:29]2[N:28]=[C:27]([NH2:32])[C:26]3[N:33]=[C:34]([CH2:39][O:40][CH2:41][CH3:42])[N:35]([CH2:36][CH2:37][CH3:38])[C:25]=3[C:24]=2[CH:23]=1.O>ClCCl>[NH2:32][C:27]1[C:26]2[N:33]=[C:34]([CH2:39][O:40][CH2:41][CH3:42])[N:35]([CH2:36][CH2:37][CH3:38])[C:25]=2[C:24]2[CH:23]=[C:22]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[CH:31]=[CH:30][C:29]=2[N:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 68973776HCID 68973776, compound

Product 1

HCID 58833664HCID 58833664, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutyryl chloride (0.236 mL, 2.25 mmol) was added dropwise, followed by triethylamine (0.2 mL, 1.4 mmol), to a stirred slurry of 8-(6-aminohexyloxy)-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-ylamine (0.900 g, 2.25 mmol) in dichloromethane (25 mL) at room temperature. After 30 minutes, water (15 mL) was added and the mixture was allowed to stir for 30 minutes. The layers were separated and the aqueous layer was extracted with dichlormethane. The organic layers were combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography (silica gel, gradient elution with 1-6% CMA in chloroform) followed by recrystallization from acetonitrile afforded 0.285 g of N-(6-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}hexyl)-2-methylpropanamide as a white crystalline solid, mp 136-138° C.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with dichlormethane
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. washby flash chromatography (silica gel, gradient elution with 1-6% CMA in chloroform)
  9. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-fef78d84cb644a02a8da3691f994c856
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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