3-Bromobenzoic acid → 3-bromo-N-cyclopropylbenzamide

HRID 1865868Notes

Reaction equation

HRID 1865868 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2[CH:22]=[CH:23][CH:24]=[N:25]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1(N)CC1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:25][CH:24]1[CH2:22][CH2:23]1)=[O:7]

Participants

6

Reactant 4

HCID 114563-Bromobenzoic acidHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 8961523-bromo-N-cyclopropylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromo-benzoic acid (2.5518 g, 12.7 mmol) and HATU (5.2230 g, 13.7 mmol) were dissolved in DMF (40 mL). DIEA (4.644 mL, 26.7 mmol) was added, and the mixture was allowed to stir at room temperature for 15 minutes. Then cyclopropylamine (0.88 mL, 12.7 mmol) was added, and the reaction was stirred at ambient temperature overnight. The solvent was removed, and the crude was purified via silica gel chromatography to yield the desired product.

Workup

  1. stirringthe reaction was stirred at ambient temperature overnight
  2. customThe solvent was removed
  3. customthe crude was purified via silica gel chromatography

Sources & evidence

ORD record
ord-eef00b8291a64ab78156c18229ef1146
Source dataset
uspto-grants-2009_12
Patent number
US07629340B2

Reaction notes

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