3-Morpholinobenzaldehyde → (1S,2S,3R,4R)-3-[6-Bromo-2-(3-morpholin-4-yl-phenyl)-3H-imidazo[4,5-b]pyridin-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

HRID 591967

Reaktionsgleichung

Reaktionsgleichung von HRID 591967
[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.[N:21]1([C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=2)[CH:30]=O)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]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:30]([C:29]3[CH:32]=[CH:33][CH:34]=[C:27]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:28]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Komponenten

3

Edukt 2

HCID 71645843-MorpholinobenzaldehydeHCID 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 178513972(1S,2S,3R,4R)-3-[6-Bromo-2-(3-morpholin-4-yl-phenyl)-3H-imidazo[4,5-b]pyridin-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideAusbeute 90 %

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 3-morpholin-4-yl-benzaldehyde (24.9 mg, 0.130 mmol) were reacted to produce 54 mg (90%) of the title compound. mp: 232-234° C., 1H NMR (300 MHz, DMSO-d6): 12.90 (s, 1H), 8.24 (s, 1H), 8.19 (s, 1H), 7.97 (s, 1H), 7.92 (s, 1H), 7.66 (s, 1H), 6.95 (d, J=8 Hz, 1H), 6.41 (br s, 1H), 6.31 (br s, 1H), 5.17 (t, J=8 Hz, 1H), 3.93 (s, 3H), 3.45 (m, 1H), 3.18 (s, 1H), 2.87 (s, 1H), 2.74 (s, 1H), 2.59 (d, J=8 Hz, 1H), 2.25 (d, J=8 Hz, 1H), 1.89 (s, 1H), 1.38 (d, J=8 Hz, 1H). MS: 509, 511 (M+H), HPLC: 2.43 min (G method).

Quellen und Nachweise

ORD-Eintrag
ord-a80e2b1d6b6d4d79b244bff8b0be1e42
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238656B2

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