Dimethylformamide → 5-Chloro-4(3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepine-2yl)nicotinonitrile tris(trifluoroacetate)

HRID 75226Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20](Cl)[C:21]=1[C:22]1[NH:23][C:24]2[C:30]3[CH:31]=[CH:32][N:33]=[CH:34][C:29]=3[NH:28][C:27]3[N:35]=[CH:36][CH:37]=[CH:38][C:26]=3[C:25]=2[N:39]=1.[CH3:41][N:42](C)C=O>[C-]#N.[Zn+2].[C-]#N>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([C:21]=1[C:22]1[NH:23][C:24]2[C:30]3[CH:31]=[CH:32][N:33]=[CH:34][C:29]=3[NH:28][C:27]3[N:35]=[CH:36][CH:37]=[CH:38][C:26]=3[C:25]=2[N:39]=1)[C:41]#[N:42]

Participants

Conditions

Temperature: 175 °C

Procedure

2-(3,5-Dichloropyridin-4-yl)-3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4′,3′-f]azepine bis(trifluoroacetate) (200 mg, 0.3 mmol), zinc cyanide (231 mg, 1.97 mmol), and tetrakis-(triphenylphosphine)palladium(0) (190 mg, 0.16 mmol) were stirred in N,N-dimethylformamide and degassed for 10 minutes by bubbling with nitrogen gas. The mixture was heated in a microwave for 20 minutes at 175° C. Purification by preparative LCMS gave the desired product (25 mg, 13%). 1H NMR (DMSO-d6): δ 9.20 (d, 2H), 8.60 (m, 1H), 8.0 (m, 1H), 7.65 (m, 1H), 6.90 (m, 1H). LC/MS: 372 (M+H)+.

Workup

customdegassed for 10 minutes
customby bubbling with nitrogen gas
customPurification by preparative LCMS

Sources & evidence

ORD record: ord-3a62f0f0017841d2a965ece83ffbd761
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835423B2

Reaction notes

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