Acetic Acid → Ethyl 3-(5-(2-(([1,1'-biphenyl]-4-ylamino)methyl)phenyl)picolinamido)propanoate

HRID 405110Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

Solid NaBH(OAc)3 (214 mg, 1.0 mmol) was added to a THF solution of ethyl 3-(5-(2-formylphenyl)picolinamido)propanoate (220 mg, 0.7 mmol), [1,1′-biphenyl]-4-amine (171 mg, 1.0 mmol), and AcOH (0.04 mL, 0.7 mmol) and the resulting mixture was warmed to 40° C. After 18 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.

Workup

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

Sources & evidence

ORD record: ord-8686137dd79b40e58b8f85e46187543f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748624B2

Reaction notes

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