4-Amino-4'-chlorodiphenyl → Ethyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-6-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405180

Reaktionsgleichung

[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]=1[C:27]1[CH:28]=[CH:29][C:30]([C:33]([NH:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:34])=[N:31][CH:32]=1)=O.[Cl:43][C:44]1[CH:49]=[CH:48][C:47]([C:50]2[CH:55]=[CH:54][C:53]([NH2:56])=[CH:52][CH:51]=2)=[CH:46][CH:45]=1.C([O-])([O-])=O.[K+].[K+]>CC(O)=O.C(Cl)Cl>[Cl:43][C:44]1[CH:45]=[CH:46][C:47]([C:50]2[CH:55]=[CH:54][C:53]([NH:56][CH2:15][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]=3[C:27]3[CH:28]=[CH:29][C:30]([C:33]([NH:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:34])=[N:31][CH:32]=3)=[CH:52][CH:51]=2)=[CH:48][CH:49]=1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

Solid NaBH(OAc)3 (68 mg, 0.32 mmol) was added to a DCM solution (0.4 mL) of ethyl 3-(5-(2-formyl-6-(trifluoromethyl)phenyl)picolinamido)propanoate (50.8 mg, 0.13 mmol) and 4′-chloro-[1,1′-biphenyl]-4-amine (28.9 mg, 0.14 mmol), and AcOH (0.07 mL) and the resulting mixture was warmed to 40° C. After 45 min 5M aqueous K2CO3 was added and the resulting mixture was extracted with DCM. The combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Aufarbeitung

extractionthe resulting mixture was extracted with DCM
dry with materialThe combined organics were dried (Na2SO4)
concentrationconcentrated
custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-dcdfb6295403412cacfbe8696e3861ee
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08748624B2

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