Dimethylformamide dimethyl acetal → HCID 59506317, compound

HRID 1801489Notes

Reaction equation

[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[N:15][CH:14]=[CH:13][C:9]=3[CH2:10][C:11](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>O1CCCC1>[CH3:19][N:20](/[CH:22]=[C:10]1/[C:11](=[O:12])[C:5]2[CH:4]=[CH:3][CH:2]=[N:1][C:6]=2[NH:7][C:8]2[CH:16]=[N:15][CH:14]=[CH:13][C:9]/1=2)[CH3:21]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 6,11-dihydro-5H-dipyrido[2,3-b:4′,3′-f]azepin-5-one (as described in WO 2007038215) (0.38 g) and dimethylformamide dimethylacetal (1.5 mL) in tetrahydrofuran (10 mL) were heated at 60° C. under nitrogen for 24 hours. Additional dimethylformamide dimethylacetal (2 mL) was then added and the mixture heated at 60° C. under nitrogen for an additional 48 hours. The reaction mixture was cooled and solvent removed under reduced pressure to give the desired product, (E)-6-((dimethylamino)methylene)-6,11-dihydro-5H-dipyrido[2,3-b:4′,3′-f]azepin-5-one (0.745 g) as a brown solid, which was used without further purification in Step 2.

Workup

temperatureThe reaction mixture was cooled
customsolvent removed under reduced pressure

Sources & evidence

ORD record: ord-78823298dbdf402cbe63be1b2fd96164
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349827B2

Reaction notes

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