Diisopropylethylamine → (S)-N3-(2-Hydroxy-1-(6-methoxypyridin-3-yl)ethyl)-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]([OH:23])=O)[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.[NH2:48][C@@H:49]([C:52]1[CH:53]=[N:54][C:55]([O:58][CH3:59])=[CH:56][CH:57]=1)[CH2:50][OH:51].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[OH:51][CH2:50][C@@H:49]([NH:48][C:21]([C:10]1[CH:11]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[CH:13]=[C:8]([C:6]([N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH3:24])=[O:7])[CH:9]=1)=[O:23])[C:52]1[CH:53]=[N:54][C:55]([O:58][CH3:59])=[CH:56][CH:57]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 5-(isobutyl(methyl)carbamoyl)-4′-methylbiphenyl-3-carboxylic acid (35 mg, 0.11 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (41 mg, 0.22 mmol), 1-hydroxybenzotriazole hydrate (16 mg, 0.11 mmol), CH2Cl2 (3 mL) were added (S)-2-amino-2-(6-methoxypyridin-3-yl)ethanol (27 mg, 0.16 mmol) (WO 2008/130481) and N,N-diisopropylethylamine (28 pt, 0.16 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, 30-70% MeCN/water[10 mM Et2NH]) to yield a white solid.
Workup
- concentrationconcentrated in vacuo
- customThe residue was purified by preparative HPLC (100×21.2 mm C18 column, 30-70% MeCN/water[10 mM Et2NH])
- customto yield a white solid
Sources & evidence
- ORD record
- ord-91bab574a0cd475e924e133f01be886e
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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