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

HRID 405269Notes

Reaction equation

[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:15][C:16]1[CH:17]=[C:18]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:31])=[N:28][CH:29]=2)[CH:19]=[C:20]([CH:22]=O)[CH:21]=1.[F:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:52]=[CH:51][C:50]([NH2:53])=[CH:49][CH:48]=2)=[CH:43][CH:42]=1.CC(O)=O>ClCCCl>[Cl:15][C:16]1[CH:17]=[C:18]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:31])=[N:28][CH:29]=2)[CH:19]=[C:20]([CH2:22][NH:53][C:50]2[CH:49]=[CH:48][C:47]([C:44]3[CH:45]=[CH:46][C:41]([F:40])=[CH:42][CH:43]=3)=[CH:52][CH:51]=2)[CH:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Solid NaBH(OAc)3 (106 mg, 0.50 mmol) was added to a DCE solution (10 mL) of ethyl 3-(5-(3-chloro-5-formylphenyl)picolinamido)propanoate (90 mg, 0.25 mmol), 4′-fluoro-[1,1′-biphenyl]-4-amine (47 g, 0.25 mmol), and AcOH (0.06 mL, 1.00 mmol) and the resulting mixture was heated to 50° C. After 16 h the mixture was concentrated and purified via column chromatography to yield the title compound.

Workup

concentrationAfter 16 h the mixture was concentrated
custompurified via column chromatography

Sources & evidence

ORD record: ord-2db889fccc5c440e825eb597538ca5a0
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748624B2

Reaction notes

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