Pyridine → [7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate

HRID 598298Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][C:23]([CH3:26])([OH:25])[CH3:24])[C:20]([CH2:27][OH:28])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>O>[C:35]([O:28][CH2:27][C:20]1[N:21]([CH2:22][C:23]([OH:25])([CH3:24])[CH3:26])[C:13]2[C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:19]=1)(=[O:37])[CH3:36]

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of 1-[7-benzyloxy-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (39.0 g, 0.133 mol), pyridine (390 mL), and acetic anhydride (195 mL) was heated at 35±5° C. for one hour in a reaction flask fitted with a calcium chloride drying tube. The reaction mixture was poured into a mixture of ice (2.5 kg) and deionized water and stirred for approximately 15 minutes. A precipitate formed and was isolated by filtration, washed with deionized water (500 mL), and dried under vacuum at 50° C. to provide 41.8 g of [7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate.

Workup

customfitted with a calcium chloride drying tube
customA precipitate formed
customwas isolated by filtration
washwashed with deionized water (500 mL)
customdried under vacuum at 50° C.

Sources & evidence

ORD record: ord-c1434a2777f34e4b907c7cc8ef82cbd1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897597B2

Reaction notes

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