2,6-Dimethoxybenzaldehyde → HCID 178491341, Verbindung

HRID 591985

Reaktionsgleichung

Reaktionsgleichung von HRID 591985
[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][O:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[C:24]=1[CH:25]=O>>[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:25]([C:24]3[C:27]([O:31][CH3:32])=[CH:28][CH:29]=[CH:30][C:23]=3[O:22][CH3:21])[NH:1][C:2]2=[N:3][CH:4]=1

Komponenten

3

Edukt 2

HCID 964042,6-DimethoxybenzaldehydeHCID 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 178491341HCID 178491341, VerbindungAusbeute 68,4 %

Versuchsvorschrift

In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (50 mg, 0.148 mmol) and 2,6-Dimethoxy-benzaldehyde (27 mg, 0.163 mmol) were reacted to produce 49 mg (68%) of the title compound. mp: 194-197° C., 1H NMR (300 MHz, DMSO-d6): 12.6 (s, 1H), 8.00 (s, 1H), 7.57 (s, 1H), 7.45 (t, J=8 Hz, 1H), 7.12 (s, 1H), 6.80 (d, J=8 Hz, 2H), 6.23 (br s, 1H), 6.17 (br s, 1H), 5.14 (t, J=8 Hz, 1H), 3.73 (s, 6H), 2.84 (s, 1H), 2.69 (s, 1H), 2.54 (d, J=8 Hz, 1H), 2.25 (d, J=8 Hz, 1H), 2.09 (s, 1H), 1.38 (d, J=8 Hz, 1H). MS: 484, 486 (M+H), HPLC: 2.33 min (G method)

Quellen und Nachweise

ORD-Eintrag
ord-3011aa1262a84e71a5e2c11f4184991d
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238656B2

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