Diisopropylethylamine → 2'-Cyano-5-(1,2-dihydroxyethyl)-4'-methyl-N-((6-methylpyridin-3-yl)methyl)biphenyl-3-carboxamide

HRID 1845312Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([CH:16]([OH:19])[CH2:17][OH:18])[CH:13]=[C:12]([C:20](O)=[O:21])[CH:11]=1)#[N:2].[CH3:23][C:24]1[N:29]=[CH:28][C:27]([CH2:30][NH2:31])=[CH:26][CH:25]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([CH:16]([OH:19])[CH2:17][OH:18])[CH:13]=[C:12]([C:20]([NH:31][CH2:30][C:27]2[CH:28]=[N:29][C:24]([CH3:23])=[CH:25][CH:26]=2)=[O:21])[CH:11]=1)#[N:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2′-cyano-5-(1,2-dihydroxyethyl)-4′-methylbiphenyl-3-carboxylic acid (30 mg, 0.10 mmol) in N,N-dimethylformamide (1 mL) were added (6-methylpyridin-3-yl)methanamine (35 mg, 0.26 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (100 mg, 0.26 mmol), and N,N-diisopropylethylamine (100 μL, 0.57 mmol). The reaction mixture was stirred for 16 hours at 25° C., and then purified by preparative HPLC to afford the final product as a light color solid.

Workup

custompurified by preparative HPLC

Sources & evidence

ORD record: ord-8c13fa820fa944babe9f5ebf15647704
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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