N-Methylisobutylamine → Ethyl 5-(isobutyl(methyl)carbamoyl)-4'-methylbiphenyl-3-carboxylate

HRID 1845161Notes

Reaction equation

HRID 1845161 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][NH:46][CH2:47][CH:48]([CH3:50])[CH3:49].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH2:47]([N:46]([CH3:45])[C:19]([C:8]1[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:9]=1)=[O:20])[CH:48]([CH3:50])[CH3:49]

Participants

7

Reactant 5

HCID 12249N-MethylisobutylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 581879575-(Ethoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid

Product 1

HCID 58188205Ethyl 5-(isobutyl(methyl)carbamoyl)-4'-methylbiphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (260 mg, 0.91 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (350 mg, 1.8 mmol), 1-hydroxybenzotriazole hydrate (140 mg, 0.91 mmol), CH2Cl2 (5 mL) were added N-methylisobutylamine (120 mg, 1.4 mmol) and N,N-diisopropylethylamine (0.24 mL, 1.4 mmol). The mixture was stirred at room temperature overnight, and then concentrated in vacuo. The residue was purified by silica gel column (0-60% EtOAc/hexane) to yield a syrup. LC-MS: 354.2 [M+1]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column (0-60% EtOAc/hexane)
  3. customto yield a syrup

Sources & evidence

ORD record
ord-4ddd47249de341398dd46d813e03366e
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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