4-(4-Methylpiperazin-1-yl)benzaldehyde → (1S,2S,3R,4R)-3-{6-Bromo-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-3H-imidazo[4,5-b]pyridin-7-ylamino}-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

HRID 591963

Reaktionsgleichung

Reaktionsgleichung von HRID 591963
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[C:5]([Br:20])=[CH:4][N:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1>>[Br:20][C:5]1[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])=[C:7]2[N:8]=[C:32]([C:31]3[CH:30]=[CH:29][C:28]([N:25]4[CH2:24][CH2:23][N:22]([CH3:21])[CH2:27][CH2:26]4)=[CH:35][CH:34]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Komponenten

3

Edukt 2

HCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeHCID 117701905(1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Produkt 1

HCID 178480650(1S,2S,3R,4R)-3-{6-Bromo-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-3H-imidazo[4,5-b]pyridin-7-ylamino}-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideAusbeute 49 %

Versuchsvorschrift

In a similar fashion to Compound LXXVI, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (40.0 mg, 0.118 mmol) and 4-(4-methyl-piperazin-1-yl)-benzaldehyde (26.6 mg, 0.130 mmol) were reacted to produce 30 mg (49%) of the title compound. mp: 215-218° C., 1H NMR (300 MHz, DMSO-d6): 13.02 (s, 1H), 7.99 (s, 1H), 7.97 (s, 2H), 7.73 (s, 1H), 7.20 (s, 1H), 7.07 (d, J=8 Hz, 2H), 6.99 (d, J=8 Hz, 1H), 6.37 (br s, 2H), 5.27 (t, J=8 Hz, 1H), 3.32 (s, 6H), 2.88 (s, 1H), 2.75 (s, 1H), 2.60 (d, J=7 Hz, 1H), 2.45 (br s, 4H), 2.23 (s, 4H). MS: 522, 524 (M+H), HPLC: 1.86 min (G method).

Quellen und Nachweise

ORD-Eintrag
ord-3f7729c27a3947ed9256b802717883fb
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238656B2

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