Diisopropylethylamine → 4'-Methyl-N-((6-methylpyridin-3-yl)methyl)-5-(3-morpholinopyrrolidine-1-carbonyl)biphenyl-3-carboxamide
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14](=[O:24])[NH:15][CH2:16][C:17]3[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=3)[CH:11]=[C:10]([C:25]([OH:27])=O)[CH:9]=2)=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[NH:51]1[CH2:55][CH2:54][CH:53]([N:56]2[CH2:61][CH2:60][O:59][CH2:58][CH2:57]2)[CH2:52]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:25]([N:51]3[CH2:55][CH2:54][CH:53]([N:56]4[CH2:57][CH2:58][O:59][CH2:60][CH2:61]4)[CH2:52]3)=[O:27])[CH:11]=[C:12]([C:14]([NH:15][CH2:16][C:17]3[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=3)=[O:24])[CH:13]=2)=[CH:4][CH:3]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 4′-methyl-5-((6-methylpyridin-3-yl)methylcarbamoyl)-biphenyl-3-carboxylic acid (55 mg, 0.15 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (58 mg, 0.30 mmol), 1-hydroxybenzotriazole hydrate (23 mg, 0.15 mmol), and CH2Cl2 (3 mL) were added 4-(pyrrolidin-3-yl)morpholine (48 mg, 0.30 mmol) and N,N-diisopropylethylamine (53 μL, 0.30 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, 30-60% 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, 30-60% MeCN/water[10 mM Et2NH])
- customto afford a white foam
Sources & evidence
- ORD record
- ord-3f6d796c106e47a7b9b3aebb33074ca6
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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