Methanol → HCID 15231843, compound

HRID 1779702Notes

Reaction equation

HRID 1779702 reaction equation
C1(C[N:8](CC2C=CC=CC=2)[C:9]2[C:18]3[N:19]=[C:20]([CH3:26])[N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:17]=3[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=2)C=CC=CC=1.C([O-])=O.[NH4+].CO.[OH-].[NH4+]>Cl.[OH-].[OH-].[Pd+2]>[CH3:26][C:20]1[N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:17]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=[C:9]([NH2:8])[C:18]=2[N:19]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 2723923Ammonium formate2×HCID 67758872HCID 67758872, compound

Product 1

HCID 15231843HCID 15231843, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 313Hydrochloric AcidSolvent

Procedure

N,N-Bis(phenylmethyl)-6,7,8,9-tetrahydro-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (820 mg, 1.87 mmole), palladium hydroxide on carbon (200 mg, Pearlman's catalyst), ammonium formate (472 mg, 7.48 mmole) and methanol (50 mL) were combined and heated at reflux for 48 hours. During the course of the reaction additional catalyst (200 mg) and ammonium formate (472 mg) were added. The reaction mixture was cooled to ambient temperature then filtered through a layer of celite. The filtrate was evaporated to provide a residue which was dissolved in 3N hydrochloric acid. The solution was made basic (pH 9) with ammonium hydroxide then extracted with methylene chloride (3×200 mL). The extracts were combined, washed with water, dried over magnesium sulfate then concentrated to provide 480 mg of a white solid. This solid was recrystallized from ethyl acetate to provide 260 mg of the desired product as a white solid, m.p. 170°-172° C. Analysis: Calculated for C15H22N4 +1/2H2O: %C, 68.16; %H, 8.64; %N, 21.2; Found: %C, 68.47; %H, 8.14; %N, 21.08.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. filtrationthen filtered through a layer of celite
  4. customThe filtrate was evaporated
  5. customto provide a residue which
  6. extractionthen extracted with methylene chloride (3×200 mL)
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationthen concentrated

Sources & evidence

ORD record
ord-c76b1d92f80e4047af6837373a2c089e
Source dataset
uspto-grants-1997_05
Patent number
US05627281

Reaction notes

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