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]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction was then quenched with saturated aqueous ammonium chloride
- extractionextracted with ethyl acetate
- washThe combined organic extracts were washed further with water and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate concentrated in vacuo
- 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
- Patent number
- US08889714B2
Linked notes
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