Diisopropylethylamine → 5-(3-Hydroxyazetidine-1-carbonyl)-4'-methyl-N-((2-methylpyrimidin-5-yl)methyl)biphenyl-3-carboxamide

HRID 1845184Notes

Reaction equation

HRID 1845184 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([C:8]2[CH:9]=[C:10]([C:21]([OH:23])=O)[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[CH:13]=2)=[O:7])[CH2:3]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:47][C:48]1[N:53]=[CH:52][C:51]([CH2:54][NH2:55])=[CH:50][N:49]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[OH:1][CH:2]1[CH2:5][N:4]([C:6]([C:8]2[CH:9]=[C:10]([C:21]([NH:55][CH2:54][C:51]3[CH:50]=[N:49][C:48]([CH3:47])=[N:53][CH:52]=3)=[O:23])[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)[CH:13]=2)=[O:7])[CH2:3]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21294601(2-Methylpyrimidin-5-yl)methanamineHCID 581883575-(3-Hydroxyazetidine-1-carbonyl)-4'-methylbiphenyl-3-carboxylic acid

Product 1

HCID 442230215-(3-Hydroxyazetidine-1-carbonyl)-4'-methyl-N-((2-methylpyrimidin-5-yl)methyl)biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(3-hydroxyazetidine-1-carbonyl)-4′-methylbiphenyl-3-carboxylic acid (350 mg, 1.1 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (430 mg, 2.2 mmol), 1-hydroxybenzotriazole hydrate (170 mg, 1.1 mmol), CH2Cl2 (50 mL) were added (2-methylpyrimidin-5-yl)methanamine (210 mg, 1.7 mmol) and N,N-diisopropylethylamine (0.39 mL, 2.2 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 preparative HPLC (100×21.2 mm C18 column, 20-60% MeCN/water[10 mM Et2NH]) to yield a white solid.

Workup

  1. washwashed with water and aq. Na2CO3 solution
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative HPLC (100×21.2 mm C18 column, 20-60% MeCN/water[10 mM Et2NH])
  5. customto yield a white solid

Sources & evidence

ORD record
ord-9f1c9fde0c1d4a18a97ab935ad47b3ef
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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