Cyclopropylamine → 5-bromo-N-cyclopropyl-2,3-dimethylbenzamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=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:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([NH:27][CH:26]1[CH2:24][CH2:25]1)=[O:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred DMF (0.2 M) solution of 5-bromo-2,3-dimethylbenzoic acid (1 eq.) from the previous step was added HATU (1.3 eq.), cyclopropylamine (1.2 eq.) and Hunig's base (3 eq.). The resulting reaction mixture was stirred at RT for 18 h. The reaction was then quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a white solid.
Workup
- customThe resulting reaction mixture
- customThe reaction was then quenched with saturated aqueous ammonium chloride
- extractionextracted with EtOAc
- washThe combined organic extracts were washed further with water and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate concentrated in vacuo
- customPurification of the crude product
- customthus obtained by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc→EtOAc)
Sources & evidence
- ORD record
- ord-da10b6e5a0284a9a9d55f06727581f78
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889714B2
Reaction notes
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