Sodium Carbonate → 1-Methylethyl 4-{[(4'-{[(2-hydroxyethyl)amino]sulfonyl}-4-biphenylyl)oxy]methyl}-1-piperidinecarboxylate

HRID 423494

Reaktionsgleichung

Reaktionsgleichung von HRID 423494
[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1)(=[O:7])=[O:6].Br[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC>[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]3)=[CH:22][CH:23]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 44119332(4-(N-(2-Hydroxyethyl)sulfamoyl)phenyl)boronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Produkt 1

HCID 591777811-Methylethyl 4-{[(4'-{[(2-hydroxyethyl)amino]sulfonyl}-4-biphenylyl)oxy]methyl}-1-piperidinecarboxylateAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

The title compound (25 mg, 26%) was prepared as a white solid from (4-{[(2-hydroxyethyl)amino]sulfonyl}phenyl)boronic acid (49 mg, 0.2 mmol), 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 9, Step 2, 71 mg, 0.2 mmol), Pd(PPh3)2Cl2 (50 mg, 0.07 mmol), 2M Na2CO3 (1 mL) and DME (1 mL) in a manner similar to Example 21, Step 3, and worked up in a manner similar to Example 9, Step 3. 1H NMR (400 MHz, CDCl3): δ 7.90 (d, 2H, J=8.6 Hz), 7.68 (d, 2H, J=8.6 Hz), 7.54 (d, 2H, J=8.8 Hz), 6.98 (d, 2H, J=8.9 Hz), 4.98-4.86 (m, 2H), 4.21 (bs, 2H), 3.85 (d, 2H, J=6.4 Hz), 3.75-3.69 (m, 2H), 3.19-3.12 (m, 2H), 2.84-2.74 (m, 2H), 2.05-1.95 (m, 1H), 1.90-1.80 (m, 3H), 1.37-1.27 (m, 2H), 1.25 (d, 6H, J=6.4 Hz); LRMS (ESI), m/z 477 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-d1a30e0d224b44e88e30efd01d1b98bf
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101634B2

Verknüpfte Notizen

Wird geladen…