Diisopropylethylamine → 4'-Methyl-5-(pyrrolidine-1-carbonyl)-N-(quinolin-7-ylmethyl)biphenyl-3-carboxamide

HRID 1845192

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:11]=[C:10]([C:21](O)=[O:22])[CH:9]=2)=[CH:4][CH:3]=1.[N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([CH2:34][NH2:35])[CH:32]=2)[CH:27]=[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>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:11]=[C:10]([C:21]([NH:35][CH2:34][C:31]3[CH:32]=[C:33]4[C:28]([CH:27]=[CH:26][CH:25]=[N:24]4)=[CH:29][CH:30]=3)=[O:22])[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid (17 mg, 0.055 mmol) in N,N-dimethylformamide (0.5 mL) were added quinolin-7-ylmethanamine (34 mg, 0.22 mmol) (WO 2008/130481), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (80 mg, 0.21 mmol) and N,N-diisopropylethylamine (80 μL, 0.46 mmol). The reaction mixture was stirred at 50° C. for 16 hours. LC-MS indicated the reaction was complete. The reaction mixture was purified by preparative HPLC to afford the titile compound.

Workup

customThe reaction mixture was purified by preparative HPLC
customto afford the titile compound

Sources & evidence

ORD record: ord-72a7f77af4c14f0c8ac195600c1d6d12
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Linked notes

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