(4-(N-Isopropylsulfamoyl)phenyl)boronic acid → 1-Methylethyl 4-{[(4'-{[(1-methylethyl)amino]sulfonyl}-4-biphenylyl)oxy]methyl}-1-piperidinecarboxylate

HRID 423493

Reaktionsgleichung

Reaktionsgleichung von HRID 423493
[CH3:1][CH:2]([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])[CH3:3].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>>[CH3:1][CH:2]([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])[CH3:3]

Komponenten

3

Edukt 2

HCID 44119552(4-(N-Isopropylsulfamoyl)phenyl)boronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Produkt 1

HCID 591777691-Methylethyl 4-{[(4'-{[(1-methylethyl)amino]sulfonyl}-4-biphenylyl)oxy]methyl}-1-piperidinecarboxylateAusbeute 9,9 %

Versuchsvorschrift

The title compound (9.4 mg, 8%) was prepared from (4-{[(1-methylethyl)amino]sulfonyl}phenyl)boronic acid (49 mg, 0.2 mmol) and 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 9, Step 2, 71 mg, 0.2 mmol) 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 7.89 (d, 2H, J=8.6 Hz), 7.66 (d, 2H, J=8.6 Hz), 7.54 (d, 2H, J=8.9 Hz), 6.98 (d, 2H, J=8.8 Hz), 4.97-4.87 (m, 1H), 4.28-4.18 (m, 2H), 3.85 (d, 2H, J=6.4 Hz), 3.58-3.45 (m, 1H), 2.84-2.74 (m, 2H), 2.05-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.37-1.27 (m, 3H), 1.25 (d, 6H, J=6.4 Hz), 1.11 (d, 6H, J=6.5 Hz); LRMS (ESI), m/z 475 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-7cdcff0f7408469c85a7e0d546e0a27a
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101634B2

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