Acetonitrile → HCID 21984164, compound

HRID 9478Notes

Reaction equation

HRID 9478 reaction equation
[CH3:1][CH:2]([CH3:27])[CH2:3][N:4]1[C:16]2[C:15]3[C:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=4)=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[CH:5]1.C(#[N:30])C>>[CH3:1][CH:2]([CH3:27])[CH2:3][N:4]1[C:16]2[C:15]3[C:14]([C:17]4[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH2:25][CH3:26])=[CH:21][CH:22]=4)=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:30])[C:7]=2[N:6]=[CH:5]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 219840881-(2-methylpropyl)-9-(4-propoxyphenyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 21984164HCID 21984164, compound

Procedure

The method described in Part J of Example 365 was used to oxidize and aminate 1-(2-methylpropyl)-9-(4-propoxyphenyl)-1H-imidazo[4,5-c]quinoline (1.1 g, 3.1 mmol). The amination reaction was stirred for 36 hours. The crude product was purified by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 70:30) to provide an oil, which was stirred with acetonitrile to provide a solid. The solid was isolated by filtration and recrystallized from acetonitrile to provide 165 mg of 1-(2-methylpropyl)-9-(4-propoxyphenyl)-1H-imidazo[4,5-c]quinolin-4-amine as light tan needles, mp 181–182° C.

Workup

  1. customThe amination reaction
  2. customThe crude product was purified by HPFC (
  3. washeluting with chloroform
  4. customCMA in a gradient from 100:0 to 70:30) to provide an oil, which
  5. customto provide a solid
  6. customThe solid was isolated by filtration
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-5de5ae4e1a584a48b0d2e3a218983a7a
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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