Dimethylformamide dimethyl acetal → (E)-9-(3-(dimethylamino)acryloyl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 926307Notes

Reaction equation

[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][N:8]1[C:18](=[O:19])[CH2:17][NH:16][C:15](=[O:20])[CH:14]=[C:9]12)(=[O:3])[CH3:2].[CH3:21][N:22]([CH:24](OC)OC)[CH3:23]>CN(C=O)C>[CH3:21][N:22]([CH3:24])[CH:23]=[CH:2][C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][N:8]1[C:18](=[O:19])[CH2:17][NH:16][C:15](=[O:20])[CH:14]=[C:9]12)=[O:3]

Participants

Conditions

Temperature: 100 °C

Procedure

100-2. A mixture of 9-acetyl-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (200 mg, 0.74 mmol) in DMF (1.0 mL) was treated with DMF-DMA (0.12 mL, 0.89 mmol) and stirred at 100° C. for 1 h. The mixture was concentrated in vacuo and the crude product obtained was purified by flash chromatography (SiO2, DCM/MeOH 98:2 to 85:15) to give the title compound (135 mg) as a beige solid. UPLC-MS: MS 236.2 (M+H+), UPLC rt 0.54 min.

Workup

concentrationThe mixture was concentrated in vacuo
customthe crude product obtained
customwas purified by flash chromatography (SiO2, DCM/MeOH 98:2 to 85:15)

Sources & evidence

ORD record: ord-40db0a8817334757aa0bb448f0d4eedb
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284331B2

Reaction notes

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