Diisopropylethylamine → N3-((6-Chloropyridin-3-yl)methyl)-N5-isobutyl-N5,4'-dimethylbiphenyl-3,5-dicarboxamide

HRID 1845164Notes

Reaction equation

HRID 1845164 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].CCN=C=NCCCN(C)C.Cl.O.ON1C2C=CC=CC=2N=N1.[Cl:48][C:49]1[CH:54]=[CH:53][C:52]([CH2:55][NH2:56])=[CH:51][N:50]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:48][C:49]1[N:50]=[CH:51][C:52]([CH2:55][NH:56][C:21]([C:10]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[CH:13]=[C:8]([C:6]([N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH3:24])=[O:7])[CH:9]=2)=[O:22])=[CH:53][CH:54]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 581880895-(Isobutyl(methyl)carbamoyl)-4'-methylbiphenyl-3-carboxylic acid

Product 1

HCID 44205230N3-((6-Chloropyridin-3-yl)methyl)-N5-isobutyl-N5,4'-dimethylbiphenyl-3,5-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(isobutyl(methyl)carbamoyl)-4′-methylbiphenyl-3-carboxylic acid (21 mg, 0.064 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (25 mg, 0.13 mmol), 1-hydroxybenzotriazole hydrate (9.9 mg, 0.064 mmol), and CH2Cl2 (3 mL) were added 2-chloro-5-aminomethylpyridine (14 mg, 0.097 mmol) and N,N-diisopropylethylamine (17 μL, 0.097 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, 40-80% MeCN/water[10 mM Et2NH]) to yield a white foam.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative HPLC (100×21.2 mm C18 column, 40-80% MeCN/water[10 mM Et2NH])
  3. customto yield a white foam

Sources & evidence

ORD record
ord-0c6d34ffbceb42c4a2ce4f37b0be6833
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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