1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22249277, compound

HRID 1815200Notes

Reaction equation

HRID 1815200 reaction equation
F[C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[C:4]([F:11])[N:3]=1.[C:12](NC1C=CC=CC=1)([CH3:15])([CH3:14])[CH3:13].[CH:23]1[CH:24]=[CH:25][C:26]2[N:31](O)N=N[C:27]=2[CH:28]=1.[CH3:33][CH2:34][N:35]=C=NCCCN(C)C.CC[N:46]([CH:50]([CH3:52])C)[CH:47]([CH3:49])C>C(Cl)Cl>[C:12]([C:23]1[CH:28]=[CH:27][C:26]([NH:31][C:8]([C:7]2[C:2]([NH:35][CH2:34][C:33]3[CH:49]=[CH:47][N:46]=[CH:50][CH:52]=3)=[N:3][C:4]([F:11])=[CH:5][CH:6]=2)=[O:10])=[CH:25][CH:24]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 254260N-(1,1-Dimethylethyl)benzenamineHCID 105830702,6-Difluoropyridine-3-carboxylic acid

Product 1

HCID 22249277HCID 22249277, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,6-difluoropyridine-3-carboxylic acid (3.2 g, 20 mmol), t-butylaniline (3.0 g, 20 mmol), HOBt (2.6 g, 20 mmol), EDAC (8 g, 40 mmol), and DIEA (8 mL) in CH2Cl2 (80 mL) was stirred at RT for 1 h. The mixture was washed with aq. NaHCO3 and brine. The organic solution was dried over Na2SO4 and concentrated in vacuo The residue was purified via flash chromatography on silica (Hex:EtOAc=4:1) to give a light yellow flaky crystal as desired product.

Workup

  1. washThe mixture was washed with aq. NaHCO3 and brine
  2. dry with materialThe organic solution was dried over Na2SO4
  3. concentrationconcentrated in vacuo The residue
  4. customwas purified via flash chromatography on silica (Hex:EtOAc=4:1)

Sources & evidence

ORD record
ord-3688016eedbb4164b3ff70349eaa03f8
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

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