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

HRID 606101Notes

Reaction equation

HRID 606101 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[CH2:44][CH2:45][CH3:46])[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[CH2:44][CH2:45][CH3:46])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 670413141-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine

Product 1

HCID 590266921-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amineYield 34.2%

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)-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine (2.62 g, 4.23 mmol) in trifluoroacetic acid (25 mL) was stirred at room temperature for 2.7 days. The solution was then worked-up and the product isolated and purified as described in Part B of Example 21 to provide 0.549 g of 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine as a white powder, mp 227.0-229.0° C.

Workup

  1. customworked-up and the product isolated
  2. custompurified

Sources & evidence

ORD record
ord-0421cece65394e0b9fd926b05b47f6ee
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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