Diisopropylethylamine → HCID 58188039, compound

HRID 1845241Notes

Reaction equation

HRID 1845241 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:11]=[C:10]([C:21](O)=[O:22])[CH:9]=2)=[CH:4][CH: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][CH:49]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:11]=[C:10]([C:21]([NH:55][CH2:54][C:51]3[CH:52]=[N:53][C:48]([CH3:47])=[CH:49][CH:50]=3)=[O:22])[CH:9]=2)=[CH:4][CH:3]=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 58188052HCID 58188052, compound

Product 1

HCID 58188039HCID 58188039, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4′-bromo-5-(pyrrolidine-1-carbonyl)-biphenyl-3-carboxylic acid (1.65 g, 4.41 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.7 g, 8.8 mmol), 1-hydroxybenzotriazole hydrate (0.20 g, 1.3 mmol), and CH2Cl2 (50 mL) were added (6-methylpyridin-3-yl)methanamine (0.81 g, 6.6 mmol) and N,N-diisopropylethylamine (1.5 mL, 8.8 mmol). The mixture was stirred at room temperature overnight and then washed with water, dried (Na2SO4), and concentrated. The residue was purified by silica gel column (0-15% MeOH/CH2Cl2) and analytical sample was purified by preparative HPLC (100×20.2 mm, C18 column; 30-80% CH3CN-water[10 mM Et2NH]) to afford a white foam.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column (0-15% MeOH/CH2Cl2) and analytical sample
  5. customwas purified by preparative HPLC (100×20.2 mm, C18 column; 30-80% CH3CN-water[10 mM Et2NH])
  6. customto afford a white foam

Sources & evidence

ORD record
ord-d29cb5886cc54263b9bb319eef518a2c
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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