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

HRID 405180

Reaction equation

[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

Participants

Conditions

Temperature: 40 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-dcdfb6295403412cacfbe8696e3861ee
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748624B2

Linked notes

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