Diisopropylethylamine → N3-(Imidazo[1,2-a]pyridin-7-ylmethyl)-N5-isobutyl-N5,4'-dimethylbiphenyl-3,5-dicarboxamide
Reaction equation
[CH2:1]([N:5]([CH3:24])[C:6]([C:8]1[CH:9]=[C:10]([C:21](O)=[O:22])[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:13]=1)=[O:7])[CH:2]([CH3:4])[CH3:3].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[N:48]1[CH:49]=[CH:50][N:51]2[CH:56]=[CH:55][C:54]([CH2:57][NH2:58])=[CH:53][C:52]=12.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[N:48]1[CH:49]=[CH:50][N:51]2[CH:56]=[CH:55][C:54]([CH2:57][NH:58][C:21]([C:10]3[CH:11]=[C:12]([C:14]4[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=4)[CH:13]=[C:8]([C:6]([N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH3:24])=[O:7])[CH:9]=3)=[O:22])=[CH:53][C:52]=12Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 5-(isobutyl(methyl)carbamoyl)-4′-methylbiphenyl-3-carboxylic acid (15 mg, 0.046 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (18 mg, 0.092 mmol), 1-hydroxybenzotriazole hydrate (7.0 mg, 0.046 mmol), and CH2Cl2 (2 mL) were added imidazo[1,2-a]pyridin-7-ylmethanamine (10 mg, 0.069 mmol) and N,N-diisopropylethylamine (12 μL, 0.069 mmol). The mixture was stirred at room temperature overnight, and then concentrated in vacuo. The residue was purified by preparative HPLC (100×21.2 mm C18 column, 40-70% MeCN/water[10 mM Et2NH]) to afford a white foam.
Workup
- concentrationconcentrated in vacuo
- customThe residue was purified by preparative HPLC (100×21.2 mm C18 column, 40-70% MeCN/water[10 mM Et2NH])
- customto afford a white foam
Sources & evidence
- ORD record
- ord-b964ffc6c91841038fec823193e4ab16
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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