Triisopropyl phosphate → 2-[2,6-Dichloro-4-(ethylthio)phenyl]-3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepine bis(trifluoroacetate)

HRID 1043482Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[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]/O)/[C:18](=O)[C:12]=2[CH:11]=[CH:10][CH:9]=1.[Cl:26][C:27]1[CH:34]=[C:33]([S:35][CH2:36][CH3:37])[CH:32]=[C:31]([Cl:38])[C:28]=1[CH:29]=O.C([O-])(=O)C.[NH4+:43].P(OC(C)C)(OC(C)C)(OC(C)C)=O>C(O)(=O)C.C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:26][C:27]1[CH:34]=[C:33]([S:35][CH2:36][CH3:37])[CH:32]=[C:31]([Cl:38])[C:28]=1[C:29]1[NH:20][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:43]=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 trifluoroacetate (200 mg, 0.4 mmol), 2,6-dichloro-4-(ethylthio)benzaldehyde (200 mg, 0.85 mmol) and ammonium acetate (0.60 g, 8.0 mmol) were stirred in acetic acid (3 mL) and heated in a microwave for 5 minutes at 130° C. Evaporation gave the crude product which was dissolved in acetonitrile (1.0 mL) and triisopropyl phosphate (100 μL, 0.4 mmol) and heated in a microwave for 5 minutes at 180° C. Purification by preparative LCMS gave the desired product LC/MS: 440 (M+H)+.

Workup

customEvaporation
customgave the crude product which
customPurification by preparative LCMS

Sources & evidence

ORD record: ord-f30c87cfc4bd441bbe55690fa7a00dc3
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563541B2

Reaction notes

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