Acetic Acid → 2-(3,5-dichloropyridin-4-yl)imidazo[4,5-d]dipyrido[2,3-b:3',4'-f]azepin-3(8H)-ol

HRID 1043462Notes

Reaction equation

[N:1]1[C:6]2[NH:7][C:8]3[CH:18]=[CH:17][N:16]=[CH:15][C:9]=3[C:10](=[N:13][OH:14])[C:11](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+:23].C(O)(=O)C.[Cl:28][C:29]1[CH:36]=[N:35][CH:34]=[C:33]([Cl:37])[C:30]=1[CH:31]=O>C([O-])(O)=O.[Na+].[Cl-].[Na+].O.O>[Cl:28][C:29]1[CH:36]=[N:35][CH:34]=[C:33]([Cl:37])[C:30]=1[C:31]1[N:13]([OH:14])[C:10]2[C:9]3[CH:15]=[N:16][CH:17]=[CH:18][C:8]=3[NH:7][C:6]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:11]=2[N:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5H-Dipyrido[2,3-b:3′,4′-f]azepine-5,6(11H)-dione 6-oxime (0.100 g, 0.416 mmol, Intermediate D-7) ammonium acetate (0.60 g, 8.0 mmol), acetic acid (2 mL), water (0.2 mL) and 3,5-dichloroisonicotinaldehyde (0.293 g, 1.66 mmol) were combined in a capped vial and heated to 80° C. for 2 h. The mixture was cooled to room temperature, and diluted with aqueous NaHCO3 and brine. The mixture was extracted three times with ethyl acetate and the combined extracts were washed with brine, dried over MgSO4, filtered, and concentrated to provide the crude intermediate product as a dark oil which was used directly in the next step. LC/MS: 397, 399 (M+H)+.

Workup

temperatureThe mixture was cooled to room temperature
extractionThe mixture was extracted three times with ethyl acetate
washthe combined extracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-284515fb875649bd83eb50313f380cac
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563541B2

Reaction notes

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