Ammonium Acetate → 2-(2,6-dichloro-4-[(triisopropylsilyl)oxy]methylphenyl)imidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepin-3(8H)-ol

HRID 1043476Notes

Reaction equation

FC(F)(F)C(O)=O.[N:8]1[C:13]2[NH:14][C:15]3[CH:25]=[N:24][CH:23]=[CH:22][C:16]=3/[C:17](=[N:20]/[OH:21])/[C:18](=O)[C:12]=2[CH:11]=[CH:10][CH:9]=1.[Cl:26][C:27]1[CH:34]=[C:33]([CH2:35][O:36][Si:37]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39])[CH:32]=[C:31]([Cl:47])[C:28]=1[CH:29]=O.C([O-])(=O)C.[NH4+:52]>C(O)(=O)C>[Cl:26][C:27]1[CH:34]=[C:33]([CH2:35][O:36][Si:37]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39])[CH:32]=[C:31]([Cl:47])[C:28]=1[C:29]1[N:20]([OH:21])[C:17]2[C:16]3[CH:22]=[CH:23][N:24]=[CH:25][C:15]=3[NH:14][C:13]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:18]=2[N:52]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A solution of (6Z)-5H-dipyrido[2,3-b:4′,3′-f]azepine-5,6(11H)-dione 6-oxime tri-fluoroacetate (1.0 g, 2.82 mmol), 2,6-dichloro-4-[(triisopropylsilyl)oxy]methylbenzaldehyde (2.04 g, 5.64 mmol) and ammonium acetate (3.3 g, 42 mmol) was stirred in acetic acid (30 mL) and heated in a microwave for 5 minutes at 130° C. Evaporation gave the crude product (1.6 g, 100%) which was used without further purification in the next step. LC/MS: 582 (M+H)+.

Workup

customEvaporation

Sources & evidence

ORD record: ord-e8100b094dfa4d2792321ca25fc3a0b8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563541B2

Reaction notes

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