Diisopropylethylamine → 5-(Hydroxy(thiazol-2-yl)methyl)-4'-methyl-N-((R)-1-(6-methylpyridin-3-yl)ethyl)biphenyl-3-carboxamide

HRID 1845300Notes

Reaction equation

[OH:1][CH:2]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)[C:3]1[CH:4]=[C:5]([C:16]([OH:18])=O)[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1.Cl.Cl.[CH3:26][C:27]1[N:32]=[CH:31][C:30]([C@H:33]([NH2:35])[CH3:34])=[CH:29][CH:28]=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>[OH:1][CH:2]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)[C:3]1[CH:4]=[C:5]([C:16]([NH:35][C@@H:33]([C:30]2[CH:31]=[N:32][C:27]([CH3:26])=[CH:28][CH:29]=2)[CH3:34])=[O:18])[CH:6]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)[CH:8]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of 5-(hydroxy(thiazol-2-yl)methyl)-4′-methylbiphenyl-3-carboxylic acid (31 mg, 0.095 mmol) in N,N-dimethylformamide (1 mL) were added (R)-1-(6-methylpyridin-3-yl)ethanamine dihydrochloride (50 mg, 0.24 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (100 mg, 0.26 mmol), and N,N-diisopropylethylamine (300 μL, 1.72 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 brown solid.

Workup

custompurified by preparative HPLC

Sources & evidence

ORD record: ord-0d9d9dd7506a4a1b8dfb5372fedcd2c5
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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