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Benzoic acid, 3,5-dibromo- → 3,5-dibromo-N-cyclopropylbenzamide

HRID 337637
Notes
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Reaction equation

HRID 337637 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2[CH:23]=[CH:24][CH:25]=[N:26]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CC1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([Br:1])[CH:10]=1)[C:5]([NH:26][CH:25]1[CH2:23][CH2:24]1)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 12063Benzoic acid, 3,5-dibromo-HCID 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 670620883,5-dibromo-N-cyclopropylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,5-dibromobenzoic acid (1 eq.) in DMF (0.15 M) was added HATU (1.3 eq.), cyclopropylamine (1.1 eq.) and Hunig's base (3 eq.). The resulting yellow mixture was stirred at RT for 18 h. The reaction was then quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Trituration of the crude product thus obtained in a mixture of ether and hexanes afforded the title compound as a white solid.

Workup

  1. customThe reaction was then quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed further with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customTrituration of the crude product thus obtained in a mixture of ether and hexanes

Sources & evidence

ORD record
ord-3e4244c5b4c2486dbba4e4862f388986
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889714B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes