Ammonia → HCID 59457842, compound

HRID 1711792Notes

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][C:3]=1[C:10]1[N:14]2[CH:15]=[C:16]([C:19]3[N:26]4[C:22]([O:23][CH:24]=[CH:25]4)=[N:21][C:20]=3[C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1.[NH4+].[OH-:35].[OH-:36].[Na+].N>O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([OH:36])=[O:35])=[CH:4][C:3]=1[C:10]1[N:14]2[CH:15]=[C:16]([C:19]3[N:26]4[C:22]([O:23][CH:24]=[CH:25]4)=[N:21][C:20]=3[C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a suspension of 4-fluoro-3-{6-[6-(4-fluorophenyl)-imidazo[2,1-b]oxazol-5-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl}-benzonitrile (0.15 g, 0.34 mmol; Example #K.1.19) in water (1 mL) and then was added NH4OH (28-30% in water, 2.0 mL, 51 mmol) and 1M NaOH (1 mL, 1.0 mmol). The reaction mixture was stirred at about 65° C. for about 8 h. Ammonia (0.5 M in 1,4-dioxane, 10 mL) was added and the reaction mixture was stirred about 72 h at about 65° C. The organic solvent was removed under reduced pressure and aqueous layer was buffered with ammonium acetate aqueous solution. The crude material was purified by reverse phase preparative chromatography (Table 1, Method e). The resulting material was purified by trituration with hot MeOH to afford the title compound (0.038 g, 23%) LC/MS (Table 1, Method a) Rt, =1.84 min; MS m/z: 458.1 (M+H)+.

Workup

stirringthe reaction mixture was stirred about 72 h at about 65° C
customThe organic solvent was removed under reduced pressure and aqueous layer
customThe crude material was purified by reverse phase preparative chromatography (Table 1, Method e)
customThe resulting material was purified by trituration with hot MeOH

Sources & evidence

ORD record: ord-caa1ace4818847279f447e9431441eec
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790741B2

Reaction notes

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