Acetic Acid → Tert-butyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

HRID 405114

Reaktionsgleichung

Reaktionsgleichung von HRID 405114
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:24]=[CH:25][C:26]([C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:30])=[N:27][CH:28]=1)=O.[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][C:51]([NH2:54])=[CH:50][CH:49]=2)=[CH:44][CH:43]=1.CC(O)=O>CCOC(C)=O.C1COCC1>[Cl:41][C:42]1[CH:43]=[CH:44][C:45]([C:48]2[CH:53]=[CH:52][C:51]([NH:54][CH2:15][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[CH:24]=[CH:25][C:26]([C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:30])=[N:27][CH:28]=3)=[CH:50][CH:49]=2)=[CH:46][CH:47]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 86754-Amino-4'-chlorodiphenylHCID 5049666Sodium triacetoxyborohydrideHCID 86674244Tert-butyl 3-(5-(2-formylphenyl)picolinamido)propanoate

Produkt 1

HCID 71060062Tert-butyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Solid NaBH(OAc)3 (90 mg, 0.42 mmol) was added to a THF solution (1.5 mL) of tert-butyl 3-(5-(2-formylphenyl)picolinamido)propanoate (100 mg, 0.28 mmol), 4′-chloro-[1,1′-biphenyl]-4-amine (86 mg, 0.42 mmol), and AcOH (16 μL, 0.28 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture diluted with EtOAc washed with water and brine, dried (Na2SO4), dry-packed onto silica gel and purified via column chromatography to yield the title compound.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry-packed onto silica gel and purified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d342f619fef245b7bbb077a55eb6b7d4
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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