Sodium Carbonate → N-Cyclopropyl-4'-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-4-biphenylcarboxamide

HRID 423475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423475
[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1.Br[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]3[O:35][N:34]=[C:33]([CH:36]([CH3:38])[CH3:37])[N:32]=3)[CH2:27][CH2:26]2)=[CH:19][CH:18]=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>[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH:25]4[CH2:30][CH2:29][N:28]([C:31]5[O:35][N:34]=[C:33]([CH:36]([CH3:38])[CH3:37])[N:32]=5)[CH2:27][CH2:26]4)=[CH:21][CH:22]=3)=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2773359(4-(Cyclopropylcarbamoyl)phenyl)boronic acidHCID 666732104-{[(4-Bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine

Produkt 1

HCID 59177785N-Cyclopropyl-4'-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-4-biphenylcarboxamideAusbeute 9,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

The title compound (9 mg, 5%) was prepared as a white solid from {4-[(cyclopropylamino)carbonyl]phenyl}boronic acid (41 mg, 0.2 mmol), 4-{[(4-bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine (prepared as in Example 24, Step 1, 76 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 7.78 (d, 2H, J=8.6 Hz), 7.59 (d, 2H, J=8.6 Hz), 7.54 (d, 2 H, J=8.8 Hz), 6.96 (d, 2H, J=8.8 Hz), 6.26 (s, 1H), 4.28-4.18 (m, 2H), 3.88 (d, 2H, J=6.2 Hz), 3.17-3.07 (m, 2H), 2.98-2.84 (m, 2H), 2.13-2.02 (m, 1H), 2.05-1.92 (m, 2H), 1.55-1.40 (m, 2H), 1.29 (d, 6H, J=6.9 Hz), 0.94-0.84 (m, 2H), 0.67-0.60 (m, 2H); LRMS (ESI), m/z 461 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-ad80766b0f3e4001b7417a9cee11f4cd
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101634B2

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