Triethylamine → HCID 68815861, compound

HRID 732471Notes

Reaction equation

HRID 732471 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.CN(C)CCCN=C=NCC.ON1C(=O)CCC1=O.[CH2:31]([NH:34][CH2:35][CH2:36][CH3:37])[CH2:32][CH3:33].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([N:34]([CH2:35][CH2:36][CH3:37])[CH2:31][CH2:32][CH3:33])=[O:7]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 8902DipropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 705093-Bromo-4-fluorobenzoic acidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 68815861HCID 68815861, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 3-bromo-4-fluorobenzoic acid (5.0 g, 22.8 mmol) with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (4.4 g, 22.8 mmol) and N-hydroxy-succinimide (2.6 g, 22.8 mmol) in dichloromethane (75 mL) and stir at room temperature for 30 min. Add N,N-dipropylamine (4.7 mL, 34.3 mmol) and triethylamine (8.0 mL, 57.1 mol) and stir at room temperature overnight. Dilute with ethyl acetate and wash with 1 N HCl, saturated aqueous potassium carbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes) to give the title compound.

Workup

  1. washwash with 1 N HCl, saturated aqueous potassium carbonate, saturated aqueous sodium chloride
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-743a781b1bbf4f8b8ad66e5326ae905e
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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