Acetic Anhydride → HCID 69507018, compound

HRID 540961Notes

Reaction equation

HRID 540961 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:24]N3CCCCC3)=[CH:5][C:4]=2[N:3]=1.C(O[C:35](=[O:37])[CH3:36])(=O)C>ClCCl>[C:35]([N:3]1[CH2:4][CH2:9][CH2:10][CH2:11][CH:2]1[O:24][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:13]([CH2:20][O:21][CH2:22][CH3:23])=[N:12][C:11]=3[C:2]([NH2:1])=[N:3][C:4]=2[CH:5]=1)(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 69506981HCID 69506981, compound

Product 1

HCID 69507018HCID 69507018, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-Amino-2-(ethoxymethyl)-7-(piperidinyloxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (from Part A) was slurried in dichloromethane (11 mL). Acetic anhydride (0.105 mL, 1.03 mmol) was added and the reaction was stirred for 16 hours. The reaction mixture was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 2-25% CMA in chloroform). The resulting solid was covered with diethyl ether for one week. Filtration of the solid provided 0.130 g of 1-[7-[(1-acetylpiperidinyl)oxy]-4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as red-tan crystals, mp 162-164° C.

Workup

  1. customThe reaction mixture was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 2-25% CMA in chloroform)
  2. waitThe resulting solid was covered with diethyl ether for one week
  3. filtrationFiltration of the solid

Sources & evidence

ORD record
ord-799b158d30f4445dbfe77aad99ae95a7
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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