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

HRID 606099Notes

Reaction equation

HRID 606099 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][N:14]3[C:22]4[C:21]([CH3:23])=[C:20]([CH3:24])[N:19]=[C:18]([N:25](CC5C=CC(OC)=CC=5)CC5C=CC(OC)=CC=5)[C:17]=4[N:16]=[C:15]3[CH3:44])[O:10][N:9]=2)=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][N:14]3[C:22]4[C:21]([CH3:23])=[C:20]([CH3:24])[N:19]=[C:18]([NH2:25])[C:17]=4[N:16]=[C:15]3[CH3:44])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 670413381-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Product 1

HCID 590266721-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amineYield 26.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Under a nitrogen atmosphere, a solution of 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine (1.48 g, 2.50 mmol) in trifluoroacetic acid (20 g) was stirred at room temperature for 24 hours. The solution was then worked-up and the product isolated as described in Part B of Example 21. After the desired product was collected by filtration, it was purified by column chromatography on silica gel (60 g, eluting with 5% to 10% CMA in chloroform) to provide 0.235 g of 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine as a white powder, mp 278.0-279.0° C.

Workup

  1. customworked-up and the product isolated
  2. filtrationAfter the desired product was collected by filtration, it
  3. customwas purified by column chromatography on silica gel (60 g, eluting with 5% to 10% CMA in chloroform)

Sources & evidence

ORD record
ord-ddc46204981a4838a2d4a6c16874a4fe
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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