4-Chlorobenzoic Acid → (S)-4-Chloro-N-(3-methyl-1-(pyrrolidin-1-yl)butan-2-yl)benzamide

HRID 1808788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808788
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:42][CH:43]([CH3:52])[C@H:44]([NH2:51])[CH2:45][N:46]1[CH2:50][CH2:49][CH2:48][CH2:47]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:51][C@@H:44]([CH:43]([CH3:52])[CH3:42])[CH2:45][N:46]2[CH2:50][CH2:49][CH2:48][CH2:47]2)=[O:8])=[CH:9][CH:10]=1

Komponenten

6

Edukt 4

HCID 63184-Chlorobenzoic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22689455(S)-3-methyl-1-(pyrrolidin-1-yl)butan-2-amine

Produkt 1

HCID 67773300(S)-4-Chloro-N-(3-methyl-1-(pyrrolidin-1-yl)butan-2-yl)benzamideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Chlorobenzoic acid (1.061 g, 6.78 mmol), TBTU (2.25 g, 7.01 mmol) and DIPEA (20.3 mmol) was mixed in DMF (25 mL). After 10 min was (S)-3-methyl-1-(pyrrolidin-1-yl)butan-2-amine (0.962 g, 6.16 mmol), which is commercially available, added. The resultant mixture was stirred at rt over night. The mixture was concentrated and the residue was purified by preparative HPLC to give the title compound (1.48 g, 82%). 1H NMR (400 MHz, CDCl3) δ 0.97, 1.80, 1.94-2.32, 2.47-2.76, 2.80-3.01, 4.13, 6.66, 7.41, 7.80. Total no of protons: 23. LCMS (M+H)+: 295.

Aufarbeitung

  1. additionadded
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5ce8fec5258341edb563d9894ae8601f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08361998B2

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