Pyrrolidine → 4'-Methyl-N-((2-methylpyrimidin-5-yl)methyl)-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxamide

HRID 1845174Notes

Reaction equation

HRID 1845174 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14](=[O:24])[NH:15][CH2:16][C:17]3[CH:18]=[N:19][C:20]([CH3:23])=[N:21][CH:22]=3)[CH:11]=[C:10]([C:25](O)=[O:26])[CH:9]=2)=[CH:4][CH:3]=1.Cl.CN(C)[CH2:31][CH2:32][CH2:33][N:34]=[C:35]=NCC.O.ON1C2C=CC=CC=2N=N1.N1CCCC1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:25]([N:34]3[CH2:35][CH2:31][CH2:32][CH2:33]3)=[O:26])[CH:11]=[C:12]([C:14]([NH:15][CH2:16][C:17]3[CH:18]=[N:19][C:20]([CH3:23])=[N:21][CH:22]=3)=[O:24])[CH:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 581879464'-Methyl-5-((2-methylpyrimidin-5-yl)methylcarbamoyl)-biphenyl-3-carboxylic acid

Product 1

HCID 442230034'-Methyl-N-((2-methylpyrimidin-5-yl)methyl)-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4′-methyl-5-((2-methylpyrimidin-5-yl)methylcarbamoyl)-biphenyl-3-carboxylic acid (11 mg, 0.030 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (12 mg, 0.061 mmol), 1-hydroxybenzotriazole hydrate (4.7 mg, 0.030 mmol), and CH2Cl2 (2 mL) were added pyrrolidine (3.2 mg, 0.046 mmol) and N,N-diisopropylethylamine (11 μL, 0.061 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, 30-70% 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, 30-70% MeCN/water[10 mM Et2NH])
  3. customto afford a white foam

Sources & evidence

ORD record
ord-46c4aa79db044c6d9b851134db1a79e6
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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