Diisopropylethylamine → (R)-N3-Isobutyl-N3,4'-dimethyl-N5-(1-(2-methylpyrimidin-5-yl)ethyl)biphenyl-3,5-dicarboxamide

HRID 1845169Notes

Reaction equation

HRID 1845169 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.[CH3:48][C:49]1[N:54]=[CH:53][C:52]([C@H:55]([NH2:57])[CH3:56])=[CH:51][N:50]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH2:1]([N:5]([CH3:24])[C:6]([C:8]1[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[CH:11]=[C:10]([C:21]([NH:57][C@@H:55]([C:52]2[CH:51]=[N:50][C:49]([CH3:48])=[N:54][CH:53]=2)[CH3:56])=[O:23])[CH:9]=1)=[O:7])[CH:2]([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 55281681(R)-1-(2-Methyl-5-pyrimidinyl)ethanamineHCID 581880895-(Isobutyl(methyl)carbamoyl)-4'-methylbiphenyl-3-carboxylic acid

Product 1

HCID 58188066(R)-N3-Isobutyl-N3,4'-dimethyl-N5-(1-(2-methylpyrimidin-5-yl)ethyl)biphenyl-3,5-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (R)-1-(2-methylpyrimidin-5-yl)ethanamine (9.5 mg, 0.069 mmol) (WO 2008/130481) 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

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative HPLC (100×21.2 mm C18 column, 40-70% MeCN/water[10 mM Et2NH])
  3. customto afford a white foam

Sources & evidence

ORD record
ord-80f4d51820284b4f90e077c0dee3b5cc
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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