1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86666272, compound

HRID 1026241Notes

Reaction equation

HRID 1026241 reaction equation
CCN=C=NCCCN(C)C.Cl.[CH3:13][NH:14][O:15][CH3:16].[Br:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH:26]2[CH2:28][CH2:27]2)[CH:21]=[CH:20][C:19]=1[CH2:29][C:30]([OH:32])=O.C1C=CC2N(O)N=NC=2C=1>C(#N)C.C(N(CC)CC)C>[Br:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH:26]2[CH2:27][CH2:28]2)[CH:21]=[CH:20][C:19]=1[CH2:29][C:30]([N:14]([O:15][CH3:16])[CH3:13])=[O:32]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 67777753HCID 67777753, compound

Product 1

HCID 86666272HCID 86666272, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

WSC (4.89 g) was added to a solution of N,O-dimethylhydroxyamine hydrochloride (2.49 g), [2-bromo-4-(cyclopropylmethoxy)phenyl]acetic acid (4.85 g), HOBt (3.91 g) and triethylamine (3.56 mL) in acetonitrile (100 mL), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The mixture was washed with 1M hydrochloric acid, water, saturated sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, passed through an NH silica gel pad, and the solvent was evaporated under reduced pressure to give the title compound (4.78 g). MS (ESI+): [M+H]+ 328.0.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe mixture was washed with 1M hydrochloric acid, water, saturated sodium hydrogen carbonate and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4b6d00adc37e4dfc918ff6e4ed47f1f7
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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