1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59463177, compound

HRID 1712965Notes

Reaction equation

HRID 1712965 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])[NH:9][N:8]=1.[C:19]([O:23][C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[S:38][C:37]([C:39](O)=[O:40])=[CH:36][CH:35]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20].CCN=C=NCCCN(C)C>C(Cl)Cl>[OH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:10]1[N:9]([C:39]([C:37]2[S:38][C:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[CH2:27][NH:26][C:24](=[O:25])[O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:35][CH:36]=2)=[O:40])[N:8]=[C:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[CH2:11]1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 59463103HCID 59463103, compoundHCID 59463233HCID 59463233, compound

Product 1

HCID 59463177HCID 59463177, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(3-pyrazin-2-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (0.10 g, 4.2 mmol), 5-(2-([(tert-butoxycarbonyl)amino]methyl)phenyl)thiophene-2-carboxylic acid (0.134 g, 4.02 mmol), and EDCI (0.116 g, 6.06 mmol) in DCM (4 mL) was allowed to stir at rt for 6 h. The reaction was quenched by the addition of water and the organic and aqueous solutions were separated. The aqueous solution was extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl [2-(5-{[5-(2-hydroxyphenyl)-3-pyrazin-2-yl-4,5-dihydro-1H-pyrazol-1-yl]carbonyl}-2-thienyl)benzyl]carbamate (0.50 g, 23%). LCMS: (FA) ES+ 556.2.

Workup

  1. customThe reaction was quenched by the addition of water
  2. customthe organic and aqueous solutions were separated
  3. extractionThe aqueous solution was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7b2d0f14c56d424c913d70b64b1a2b7f
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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