2-Ethyl-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine → 2-ethyl-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

HRID 606097Notes

Reaction equation

HRID 606097 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:33][C:34]2[O:38][N:37]=[C:36]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[CH:35]=2)[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]=[C:7]([N:13](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[C:6]=2[N:32]=1)[CH3:2]>FC(F)(F)C(O)=O>[CH2:1]([C:3]1[N:4]([CH2:33][C:34]2[O:38][N:37]=[C:36]([C:39]3[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=3)[CH:35]=2)[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]=[C:7]([NH2:13])[C:6]=2[N:32]=1)[CH3:2]

Participants

3

Reactant 1

HCID 670413072-Ethyl-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Product 1

HCID 590266842-ethyl-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amineYield 42.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a solution of 2-ethyl-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (2.52 g, 4.16 mmol) in trifluoroacetic acid (25 g) was stirred at room temperature for 20 hours. The trifluoroacetic acid was removed under reduced pressure, and the resulting red oil was stirred with aqueous hydrochloric acid (25 mL of 6 N) and ethanol (10 mL) for 30 minutes. The resulting mixture filtered to remove a solid impurity, cooled to 0° C., adjusted to pH 14 with the addition of 50% (w/w) aqueous sodium hydroxide, and stirred at for 30 minutes. A solid was present and was isolated by filtration and purified by sequential trituration with toluene, trituration with diethyl ether, and recrystallization from acetonitrile to provide 0.6488 g of 2-ethyl-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine as a white flocculant solid, mp 255.0-256.0° C.

Workup

  1. customThe trifluoroacetic acid was removed under reduced pressure
  2. filtrationThe resulting mixture filtered
  3. customto remove a solid impurity
  4. additionadjusted to pH 14 with the addition of 50% (w/w) aqueous sodium hydroxide
  5. stirringstirred at for 30 minutes
  6. customwas isolated by filtration
  7. custompurified by sequential trituration with toluene, trituration with diethyl ether, and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-a2f5a92b03dc44368a92485ba6c93370
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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