2,6-Diethylaniline → HCID 178436232, compound

HRID 1406003Notes

Reaction equation

HRID 1406003 reaction equation
[O:1]=[C:2]1[C:8]2[NH:9][N:10]=[C:11]([C:12]([OH:14])=O)[C:7]=2[CH2:6][CH2:5][CH2:4][CH2:3]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH2:36]([C:38]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][CH3:46])[C:39]=1[NH2:40])[CH3:37].CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:36]([C:38]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][CH3:46])[C:39]=1[NH:40][C:12]([C:11]1[C:7]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[C:8]=2[NH:9][N:10]=1)=[O:14])[CH3:37]

Participants

8

Reactant 5

HCID 113692,6-DiethylanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178524939HCID 178524939, compound

Product 1

HCID 178436232HCID 178436232, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 8-oxo-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxylic acid (0.045 g, 0.232 mmol) in anhydrous DMF (2 mL) was treated with HOBt (0.047 g, 0.347 mmol), EDCI (0.065 g, 0.347 mmol), 2,6-diethylaniline (0.253 mL, 0.925 mmol) and DIPEA (0.188 mL, 1.390 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with water, extracted with AcOEt (2×20 mL). The organic fractions were combined, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (eluant: AcOEt/hexane 2/8) provided 0.027 g (35% yield) of the title compound.

Workup

  1. extractionextracted with AcOEt (2×20 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (eluant: AcOEt/hexane 2/8)

Sources & evidence

ORD record
ord-da3849d77ffb4bb3aa8e1820718bf244
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

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