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

HRID 606092Notes

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]=[CH:15]3)[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]=[CH:15]3)[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (2.0 g, 3.5 mmol) in trifluoroacetic acid (20 mL) was stirred at room temperature for 16 hours. The trifluoroacetic acid was removed under reduced pressure, and the residue was triturated with aqueous hydrochloric acid (25 mL of 6 N) and ethanol (20 mL) for 30 minutes. The resulting mixture was adjusted to pH 14 with the addition of 50% (w/w) aqueous sodium hydroxide and stirred at 0° C. for 30 minutes. A solid was present and was isolated by filtration and purified by column chromatography on silica gel (eluting with 5% to 10% CMA in chloroform). The resulting solid was dried under high vacuum at 100° C. for 18 hours to provide 0.708 g of 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine as a white powder, mp 244.0-246.0° C.

Workup

customThe trifluoroacetic acid was removed under reduced pressure
customthe residue was triturated with aqueous hydrochloric acid (25 mL of 6 N) and ethanol (20 mL) for 30 minutes
additionThe resulting mixture was adjusted to pH 14 with the addition of 50% (w/w) aqueous sodium hydroxide
customwas isolated by filtration
custompurified by column chromatography on silica gel (eluting with 5% to 10% CMA in chloroform)
customThe resulting solid was dried under high vacuum at 100° C. for 18 hours

Sources & evidence

ORD record: ord-a95673a6fbcc41d49ab72bc5bf8cbf96
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915281B2

Reaction notes

Loading…