2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine → HCID 59026705, compound

HRID 606094Notes

Reaction equation

HRID 606094 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:35][C:36]2[O:40][N:39]=[C:38]([C:41]3[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=3)[CH:37]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([N:15](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[C:8]=2[N:34]=1)[CH3:2]>FC(F)(F)C(O)=O>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:35][C:36]2[O:40][N:39]=[C:38]([C:41]3[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=3)[CH:37]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH2:15])[C:8]=2[N:34]=1)[CH3:2]

Participants

3

Reactant 1

HCID 670414132-(ethoxymethyl)-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 59026705HCID 59026705, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (3.55 g, 5.58 mmol) in trifluoroacetic acid (30 mL) was stirred at room temperature for three days. The trifluoroacetic acid was removed under reduced pressure, and the residue was triturated with hydrochloric acid (50 mL of a 6 N in ethanol) and water (10 mL) for 30 minutes. The resulting mixture was adjusted to pH 14 with the addition of 50% (w/w) aqueous sodium hydroxide and stirred for 30 minutes. The volatiles were removed under reduced pressure, and the residue was recrystallized from aceotnitrile after a hot filtration. Three crops of crystals were collected to provide 1.35 g of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine. A portion of this material was diluted with dichloromethane. The resulting solution was washed sequentially with aqueous potassium carbonate, water, and brine; purified by column chromatography on silica gel (250 g, eluting with 15% CMA in chloroform); and dried to provide 0.657 g of an analytically pure sample as a white powder, mp 246.0-247.0° C.

Workup

  1. customThe trifluoroacetic acid was removed under reduced pressure
  2. customthe residue was triturated with hydrochloric acid (50 mL of a 6 N in ethanol) and water (10 mL) for 30 minutes
  3. additionThe resulting mixture was adjusted to pH 14 with the addition of 50% (w/w) aqueous sodium hydroxide
  4. customThe volatiles were removed under reduced pressure
  5. customthe residue was recrystallized from aceotnitrile
  6. filtrationafter a hot filtration
  7. customThree crops of crystals were collected

Sources & evidence

ORD record
ord-eb1f62df58f9440c953668ef41d67f78
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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