Diisopropylethylamine → (R)-2'-Cyano-4'-methyl-N-(1-(2-methylpyrimidin-5-yl)ethyl)-5-(thiazol-2-yloxy)biphenyl-3-carboxamide

HRID 1845283Notes

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]([O:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:13]=[C:12]([C:22](O)=[O:23])[CH:11]=1)#[N:2].[CH3:25][C:26]1[N:31]=[CH:30][C:29]([C@H:32]([NH2:34])[CH3:33])=[CH:28][N:27]=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]([O:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:13]=[C:12]([C:22]([NH:34][C@@H:32]([C:29]2[CH:28]=[N:27][C:26]([CH3:25])=[N:31][CH:30]=2)[CH3:33])=[O:23])[CH:11]=1)#[N:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2′-cyano-4′-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylic acid (30 mg, 0.089 mmol) in N,N-dimethylformamide (1 mL) were added (R)-1-(2-methylpyrimidin-5-yl)ethanamine (30 mg, 0.22 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 a brown solid.

Workup

custompurified by preparative HPLC
customto afford a brown solid

Sources & evidence

ORD record: ord-bf4e53f969314079b7516a562f9a7cde
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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