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Triethylamine → 3-(4-{4-[(1H-benzoimidazol-2-ylamino)methyl]piperidin-1-yl}phenyl)-2-(2,4,6-trimethylbenzoylamino)propionic acid

HRID 1424320
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1424320
FC(F)(F)C(O)=O.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.B([C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH:35]([NH:39][C:40](=[O:50])[C:41]2[C:46]([CH3:47])=[CH:45][C:44]([CH3:48])=[CH:43][C:42]=2[CH3:49])[C:36]([OH:38])=[O:37])=[CH:30][CH:29]=1)(O)O.CCN(CC)CC>ClCCCl.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH:35]([NH:39][C:40](=[O:50])[C:41]3[C:42]([CH3:49])=[CH:43][C:44]([CH3:48])=[CH:45][C:46]=3[CH3:47])[C:36]([OH:38])=[O:37])=[CH:30][CH:29]=2)[CH2:21][CH2:20]1
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 576609483-(4-Boronophenyl)-2-(2,4,6-trimethylbenzoylamino)propionic acidHCID 69079613(1H-benzoimidazol-2-yl)piperidin-4-ylmethylamine trifluoroacetate

Produkt 1

HCID 248721893-(4-{4-[(1H-benzoimidazol-2-ylamino)methyl]piperidin-1-yl}phenyl)-2-(2,4,6-trimethylbenzoylamino)propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895
Cupric acetate
Katalysator
HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

95 mg (0.207 mmol, calculated as bistrifluoroacetate salt) of crude piperidine derivative (19), 113 mg (0.621 mmol) Cu(OAc)2, 147 mg (0.415 mmol) boronic acid (6) and 1.72 ml (12.42 mmol) NEt3 were mixed in 10 ml DCE and stirred at room temperature for 20 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in methanol and subsequently submitted to reversed phase HPLC purification using a water/acetonitrile gradient containing 0.1% TFA. The required fractions were collected and lyophilized to yield (20) as white solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methanol
  3. customphase HPLC purification
  4. additioncontaining 0.1% TFA
  5. customThe required fractions were collected

Quellen und Nachweise

ORD-Eintrag
ord-77abbd1afe25445aa857ff55be847c6d
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08927534B2

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