Dimethylformamide → (4Z)-N,N-dimethyl-4-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]-1,3-dioxoisoquinoline-6-carboxamide

HRID 2236605

Reaktionsgleichung

Reaktionsgleichung von HRID 2236605
[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][C:9](=[O:16])[C:8]2=[CH:17]OC)=[O:4].[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][C:32](N)=[CH:31]C=2)[CH2:24][CH2:23]1.C[N:37](C)C=O>>[CH3:20][N:2]([CH3:1])[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][C:9](=[O:16])/[C:8]/2=[CH:17]\[NH:37][C:33]1[CH:34]=[CH:29][C:28]([N:25]2[CH2:24][CH2:23][N:22]([CH3:21])[CH2:27][CH2:26]2)=[CH:31][CH:32]=1)=[O:4]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 686999914-Methoxymethylene-1,3-dioxo-1,2,3,4-tetrahydro-isoquinoline-6-carboxylic acid dimethylamide

Produkt 1

HCID 178480731(4Z)-N,N-dimethyl-4-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]-1,3-dioxoisoquinoline-6-carboxamideAusbeute 86 %

Versuchsvorschrift

Prepared from a slurry of 81.7 mg (0.298 mmol) of 4-methoxymethylene-1,3-dioxo-1,2,3,4-tetrahydro-isoquinoline-6-carboxylic acid dimethylamide and 56.9 mg (0.298 mmol) of 4-(4-methylpiperazin-1-yl)methyl-phenylamine in 1.5 mL of N,N-dimethylformamide (DMF) at 100° C. under N2 as described for example 21. After heating for 0.5 h, the reaction is chilled in ice. The solid product is collected, washed with N,N-dimethylformamide (DMF) and Et2O and dried to give 111 mg (86%) of yellow crystals: mp >300° C.; 1H NMR (DMSO-d6) δ 12.55 (d, 1H, J=12.8 Hz), 11.25 (s, 1H), 8.88 (d, 1H, J=12.8 Hz), 8.14 (s, 1H), 8.03 (d, 1H, J=8.07 Hz), 7.46 (d, 2H, J=8.94), 7.16 (d, 1H, J=8.07 Hz), 6.98 (d, 2H, J=8.94 Hz), 3.14 (m, 4H), 3.04 (s, 3H), 2.90 (s, 3H), 2.46 (m, 4H), 2.22 (s, 3H); HRMS (ESI) m/e calcd for C24H27N5O3 432.20411. found 432.20337 (M+H)+1, Analysis for C24H27N5O3, Calcd: C, 66.50; H, 6.28; N, 16.16. Found: C, 66.33; H, 6.43; N, 16.28.

Aufarbeitung

  1. temperatureAfter heating for 0.5 h
  2. temperaturethe reaction is chilled in ice
  3. customThe solid product is collected
  4. washwashed with N,N-dimethylformamide (DMF) and Et2O
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a36d190e950a47cca7524713b510b86f
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713994B2

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