Diethylamine → HCID 67440216, compound

HRID 1471496Notes

Reaction equation

HRID 1471496 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:22]=[C:21]([C:23]#[N:24])[CH:20]=[CH:19][C:7]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]2[B:16]([OH:17])[O:15][CH2:14][C:13]=2[CH:18]=1)(O)=[O:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:46]([NH:48][CH2:49][CH3:50])[CH3:47]>CN(C)C1C=CN=CC=1.CN(C=O)C.O>[C:23]([C:21]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[B:16]([OH:17])[O:15][CH2:14][C:13]=3[CH:18]=2)=[C:6]([CH:22]=1)[O:5][CH2:4][C:1]([N:48]([CH2:49][CH3:50])[CH2:46][CH3:47])=[O:2])#[N:24]

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 67439337HCID 67439337, compound

Product 1

HCID 67440216HCID 67440216, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-[2-(Carboxymethoxy)-4-cyanophenoxy]-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (D17) (1.00 g, 3.08 mmol), EDCI (1.77 g, 9.24 mmol), HOBT (1.25 g, 9.24 mmol), diethylamine (0.96 mL, 9.24 mmol), and 4-dimethylaminopyridine (75 mg, 0.62 mmol) in DMF (20 mL) was stirred at room temperature overnight. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified with silica gel chromatography (9:1 chloroform/methanol). The combined fractions were put under reduced pressure to remove solvent and then washed with water and toluene. The solvent was again removed under reduced pressure. Another silica gel chromatography column was used (5:5 acetone:hexane). The desired fractions were combined and the solvent was removed under reduced pressure. The residue was recrystallized using hexanes and diisopropylether. Pure 2-(5-cyano-2-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)phenoxy)-N,N-diethylacetamide (0.662 g, 57%) was obtained.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified with silica gel chromatography (9:1 chloroform/methanol)
  6. customto remove solvent
  7. washwashed with water and toluene
  8. customThe solvent was again removed under reduced pressure
  9. customthe solvent was removed under reduced pressure
  10. customThe residue was recrystallized

Sources & evidence

ORD record
ord-6516e682566b49eb8fe5f3d40d0566ae
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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