Acetic Anhydride → HCID 58869121, compound

HRID 1623200Notes

Reaction equation

HRID 1623200 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.C(N(CC)CC)C.Cl.[OH:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[C:26]([NH2:35])[C:25]=2[N:24]=[C:23]1[CH2:36][CH2:37][CH3:38].[OH-].[Na+].C(=O)(O)[O-].[Na+].O>ClCCl>[NH2:35][C:26]1[C:25]2[N:24]=[C:23]([CH2:36][CH2:37][CH3:38])[N:22]([CH2:21][CH2:20][CH2:19][CH2:18][N:17]([OH:16])[C:5](=[O:7])[CH3:6])[C:34]=2[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N:27]=1

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 86585896Sodium bicarbonate waterHCID 86612264HCID 86612264, compound

Product 1

HCID 58869121HCID 58869121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.490 mL, 5.14 mmol) and triethylamine (2.86 mL, 20.6 mmol) were added to a solution of 1-[4-(hydroxyamino)butyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride (1.80 g, 5.14 mmol) in dichloromethane (50 mL). The reaction mixture was stirred at room temperature for 2 hours, then 10% aqueous sodium hydroxide was added. The mixture was stirred for 1 hour, then was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, gradient elution with 10-20% methanol in dichloromethane). The appropriate fractions were combined and concentrated under reduced pressure to afford a solid that was slurried in 1:1 saturated aqueous sodium bicarbonate/water, filtered, washed with water, and dried to yield N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-hydroxyacetamide as brown needles, mp 191-193° C.

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (silica gel, gradient elution with 10-20% methanol in dichloromethane)
  4. concentrationconcentrated under reduced pressure
  5. customto afford a solid
  6. filtrationfiltered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-b4afc71ea77345f58283074610684f29
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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