(4-(Cyclopentylcarbamoyl)phenyl)boronic acid → 1-Methylethyl 4-[({4'-[(cyclopentylamino)carbonyl]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423487

Reaktionsgleichung

Reaktionsgleichung von HRID 423487
[CH:1]1([NH:6][C:7]([C:9]2[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)=[CH:21][CH:20]=1>>[CH:1]1([NH:6][C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH:27]4[CH2:28][CH2:29][N:30]([C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:32]4)=[CH:23][CH:24]=3)=[CH:11][CH:10]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

3

Edukt 2

HCID 2773358(4-(Cyclopentylcarbamoyl)phenyl)boronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Produkt 1

HCID 591777671-Methylethyl 4-[({4'-[(cyclopentylamino)carbonyl]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylateAusbeute 15,1 %

Versuchsvorschrift

The title compound (14 mg, 12%) was prepared from {4-[(cyclopentylamino)carbonyl]phenyl}boronic acid (47 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 7.78 (d, 2H, J=8.4 Hz), 7.59 (d, 2H, J=8.4 Hz), 7.53 (d, 2H, J=8.8 Hz), 6.96 (d, 2H, J=8.8 Hz), 6.04 (d, 1 H, J=7.4 Hz), 4.97-4.86 (m, 1H), 4.48-4.37 (m, 1H), 4.21 (bs, 2H), 3.85 (d, 2H, J=6.4 Hz), 2.83-2.73 (m, 2H), 2.17-2.06 (m, 2H), 2.05-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.78-1.62 (m, 4H), 1.55-1.45 (m, 2H), 1.35-1.26 (m, 2H), 1.24 (d, 6H, J=6.2 Hz); LRMS (ESI), m/z 465 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-15ff733f32894814a8bc13cd651bc980
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101634B2

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