Cyclopropylamine → 3,5-dibromo-N-cyclopropyl-4-methylbenzamide

HRID 337625Notes

Reaction equation

HRID 337625 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:12])[C:10]=1[CH3:11])[C:5]([OH:7])=O.CN(C(ON1N=NC2[CH:24]=[CH:25][CH:26]=[N:27]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:12][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([Br:1])[C:10]=1[CH3:11])[C:5]([NH:27][CH:26]1[CH2:24][CH2:25]1)=[O:7]

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 6704753,5-Dibromo-4-methylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 670619513,5-dibromo-N-cyclopropyl-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,5-dibromo-4-methylbenzoic acid (1 eq.) in DMF (0.4 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 an off-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-ea0f3eb7620d419284e644fe8bc865cf
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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