Diisopropylethylamine → Ethyl 4'-methyl-5-((6-methylpyridin-3-yl)methylcarbamoyl)biphenyl-3-carboxylate

HRID 1845211Notes

Reaction equation

HRID 1845211 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:19](O)=[O:20])[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:11]=1)=[O:5])[CH3:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:45][C:46]1[N:51]=[CH:50][C:49]([CH2:52][NH2:53])=[CH:48][CH:47]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[C:8]([C:19](=[O:20])[NH:53][CH2:52][C:49]3[CH:50]=[N:51][C:46]([CH3:45])=[CH:47][CH:48]=3)[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 12214337(6-Methylpyridin-3-yl)methanamineHCID 581879575-(Ethoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid

Product 1

HCID 58188105Ethyl 4'-methyl-5-((6-methylpyridin-3-yl)methylcarbamoyl)biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (1.5 g, 5.3 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.0 g, 10 mmol), 1-hydroxybenzotriazole hydrate (0.32 g, 2.1 mmol), and CH2Cl2 (50 mL) were added (6-methylpyridin-3-yl)methanamine (0.97 g, 7.9 mmol) and N,N-diisopropylethylamine (1.8 mL, 10 mmol). The mixture was stirred at room temperature for 4 h, and then washed with water and aq. Na2CO3 solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column to afford a white foam.

Workup

  1. washwashed with water and aq. Na2CO3 solution
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column
  5. customto afford a white foam

Sources & evidence

ORD record
ord-fdeb7088e57946b69fc02f3e5cfd424c
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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