Acetic Anhydride → HCID 58833706, compound

HRID 2203638Notes

Reaction equation

HRID 2203638 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][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:5][C:4]=2[N:3]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>ClCCl>[C:31]([N:28]1[CH2:29][CH2:30][CH:25]([O:24][C:6]2[CH:7]=[CH:8][C:9]3[C:10]4[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]=4[C:2]([NH2:1])=[N:3][C:4]=3[CH:5]=2)[CH2:26][CH2:27]1)(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 68969604HCID 68969604, compound

Product 1

HCID 58833706HCID 58833706, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-Amino-2-(ethoxymethyl)-7-(piperidin-4-yloxy)-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-acetylpiperidin-4-yl)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-3b1e22fc110e4661a7e799822e2c1771
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

Loading…