Triethyl orthoacetate → 7-benzyloxy-2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

HRID 540838Notes

Reaction equation

[C:1](OCC)(OCC)(OCC)[CH2:2][CH3:3].C(OCC)(OCC)(OCC)C.[CH2:24]([O:31][C:32]1[CH:41]=[C:40]2[C:35]([C:36]([NH:43][CH2:44][CH:45]([CH3:47])[CH3:46])=[C:37]([NH2:42])[CH:38]=[N:39]2)=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([O:31][C:32]1[CH:33]=[CH:34][C:35]2[C:36]3[N:43]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:1]([CH2:2][CH3:3])=[N:42][C:37]=3[CH:38]=[N:39][C:40]=2[CH:41]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

Reactant 3

HCID 66221Triethyl orthoacetate

HCID 66995Ethyl orthopropionate

HCID 670509707-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine

Product 1

HCID 670509537-benzyloxy-2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolineYield 34.3%

Procedure

The general method described in Part A of Example 9 was followed. Triethyl orthopropionate (7.66 mL, 58.1 mmol) was added in lieu of triethyl orthoacetate to a solution of 7-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine (18.68 g, 58.11 mmol) in xylenes (200 mL). At the end of the reaction, the precipitate was collected in three crops to provide 7.16 g of 7-benzyloxy-2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline as a light-brown solid, mp 127° C.

Workup

customAt the end of the reaction
customthe precipitate was collected in three crops

Sources & evidence

ORD record: ord-6888792321904e609f92000adf57704c
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871782B2

Reaction notes

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