N,N-Dimethylglycine → Benzo[d]oxazole-7-carboxamide

HRID 415310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415310
N1CCCC([C:7]2[O:8][C:9]3[C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)C1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.CN(C)CC(O)=O>C.[Cl-].[Cl-]>[O:8]1[C:9]2[C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=[CH:7]1

Komponenten

7

Edukt 5

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 666209242-(Piperidin-3-yl)benzo[d]oxazole-7-carboxamide

Produkt 1

HCID 90970678Benzo[d]oxazole-7-carboxamideAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 20976018Dichloride methaneLösungsmittel

Versuchsvorschrift

A mixture of 2-(piperidin-3-yl)benzo[d]oxazole-7-carboxamide (160 mg, 1.2 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (82.4 mg, 0.61 mmol), 1-hydroxybenzotriazole (82 mg, 0.61 mmol), triethyl amine (117 mg, 0.61 mmol), 2-(dimethylamino)acetic acid (83 mg, 0.61 mmol) were added in 50 ml dichloride methane and stirred at room temperature over night. The mixture was evaporated under reduced pressure and purified by pre-HPLC. 13 mg 2-(1-(2-dimethylamino)acetyl)piperidin-3-yl)benzo[d]oxazole-7-carboxamide was obtained. Yield 7%. 1H-NMR (400 MHz, CD3OD): δ 1.52-1.65 (m, 1H), 1.77-1.85 (m, 1H), 2.15-2.31 (m, 8H), 2.20-2.28 (m, 2H), 3.31-3.39 (m, 2H), 3.75-3.90 (m, 2H), 4.42-4.36 (m, 1H), 7.44-7.47 (m, 1H), 7.81-7.88 (m, 2H). LC-MS (ESI) m/z: 331 (M+1)+.

Aufarbeitung

  1. customThe mixture was evaporated under reduced pressure
  2. custompurified by pre-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d4a18c09fb3b4217aacbe169d92f4a22
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088760B2

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