Pyrrolidine → Methyl 2'-cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate

HRID 1845196Notes

Reaction equation

HRID 1845196 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:12]([C:20]([OH:22])=O)[CH:11]=1)#[N:2].Cl.CN(C)[CH2:26][CH2:27][CH2:28][N:29]=[C:30]=NCC.O.ON1C2C=CC=CC=2N=N1.N1CCCC1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]([C:20]([N:29]2[CH2:30][CH2:26][CH2:27][CH2:28]2)=[O:22])[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:15]=1)#[N:2]

Participants

7

Reactant 5

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 581883772'-Cyano-5-(methoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid

Product 1

HCID 58188323Methyl 2'-cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2′-cyano-5-(methoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (0.20 g, 0.68 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.26 g, 1.4 mmol), 1-hydroxybenzotriazole hydrate (0.21 g, 1.4 mmol), and methylene chloride (10 mL) were added pyrrolidine (0.072 g, 1.0 mmol) and N,N-diisopropylethylamine (0.24 mL, 1.4 mmol). The mixture was stirred at room temperature overnight, and then concentrated. The residue was purified via flash chromatography (silica gel column, 0-100% EtOAc/hexane) to afford the desired product as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified via flash chromatography (silica gel column, 0-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-f0983c482d7a4fd0bdc57da23d4164ae
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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