(R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-ol → 9-[(3R)-3-hydroxy-3-(5-methyl-1,2,4-oxadiazol-3-yl)but-1-yn-1-yl]-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7(12),8,10-pentaene-4-carboxamide

HRID 575133

Reaktionsgleichung

Reaktionsgleichung von HRID 575133
Br[C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][CH:10]([CH2:11]3)[N:9]3[C:5](=[N:6][C:7]([C:17]([NH2:19])=[O:18])=[CH:8]3)[C:4]=2[CH:3]=1.[CH3:20][C:21]1[O:25][N:24]=[C:23]([C@:26]([OH:30])([C:28]#[CH:29])[CH3:27])[N:22]=1>>[OH:30][C@:26]([C:23]1[N:22]=[C:21]([CH3:20])[O:25][N:24]=1)([CH3:27])[C:28]#[C:29][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][CH:10]([CH2:11]3)[N:9]3[C:5](=[N:6][C:7]([C:17]([NH2:19])=[O:18])=[CH:8]3)[C:4]=2[CH:3]=1

Komponenten

3

Edukt 2

HCID 86669593(R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-olHCID 8669308110-Bromo-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

Produkt 1

HCID 866931589-[(3R)-3-hydroxy-3-(5-methyl-1,2,4-oxadiazol-3-yl)but-1-yn-1-yl]-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7(12),8,10-pentaene-4-carboxamide

Versuchsvorschrift

9-Bromo-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7(12),8,10-pentaene-4-carboxamide (0.15 g) was reacted with (2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-ol similar to as described in Procedure G to afford 24.2 mg of 9-[(3R)-3-hydroxy-3-(5-methyl-1,2,4-oxadiazol-3-yl)but-1-yn-1-yl]-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7(12),8,10-pentaene-4-carboxamide following reverse phase hplc purification. MS (Q1) 390.1 (M)+. 1H NMR (400 MHz, DMSO) δ 8.65 (s, 1H), 7.84 (s, 1H), 7.52 (s, 1H), 7.30 (s, 2H), 7.09 (s, 1H), 6.72 (s, 1H), 4.98-4.88 (m, 1H), 3.78-3.68 (m, 1H), 3.15-3.02 (m, 2H), 2.62 (s, 3H), 1.85 (s, 3H), 1.66 (d, J=11.9 Hz, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-3b771afb83104ec29207ea782b1736f4
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034866B2

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