Diisopropylethylamine → 3-(5-Methylpyridin-2-yl)-N-((6-methylpyridin-3-yl)methyl)-5-(pyrrolidine-1-carbonyl)benzamide

HRID 1845225Notes

Reaction equation

HRID 1845225 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[CH:16]=2)[C:11]([OH:13])=O)=[N:6][CH:7]=1.[CH3:24][C:25]1[N:30]=[CH:29][C:28]([CH2:31][NH2:32])=[CH:27][CH:26]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[CH:16]=2)[C:11]([NH:32][CH2:31][C:28]2[CH:29]=[N:30][C:25]([CH3:24])=[CH:26][CH:27]=2)=[O:13])=[N:6][CH:7]=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 581882913-(5-Methylpyridin-2-yl)-5-(pyrrolidine-1-carbonyl)benzoic acid

Product 1

HCID 442229723-(5-Methylpyridin-2-yl)-N-((6-methylpyridin-3-yl)methyl)-5-(pyrrolidine-1-carbonyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a round-bottom flask were charged 3-(5-methylpyridin-2-yl)-5-(pyrrolidine-1-carbonyl)benzoic acid (80 mg, 0.26 mmol), (6-methylpyridin-3-yl)methanamine (60 mg, 0.49 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (90 mg, 0.47 mmol), 1-hydroxybenzotriazole hydrate (80 mg, 0.52 mmol), N,N-diisopropylethylamine (80 mg, 0.62 mmol) and methylene chloride (5 mL). The mixture was stirred at room temperature overnight and then concentrated. The residue was purified via preparative HPLC to afford the desired product as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-8e3511c561ec49a8acb1306b333f8783
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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