Citric Acid → HCID 21921391, compound

HRID 1245060Notes

Reaction equation

HRID 1245060 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=O)=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Br:50][C:51]1[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH:54]=[C:53]([NH2:61])[N:52]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.O>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:2]=[CH:3][C:4]([CH2:7][C:8]([NH:61][C:53]2[N:52]=[C:51]([Br:50])[C:60]3[C:55]([CH:54]=2)=[CH:56][CH:57]=[CH:58][CH:59]=3)=[O:10])=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 311Citric AcidHCID 3332FelbinacHCID 81531DiisopropylethylamineHCID 2898451-Bromoisoquinolin-3-amineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 21921391HCID 21921391, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-biphenylacetic acid (1.0 g, 4.7 mmol) in 10 ml of anhydrous DMF was added HBTU (2.1 g, 5.7 mmol) and 1.0 ml of DIEA. The mixture was stirred at room temperature for 10 min, and then 1-bromo-3-isoquinolinamine (0.68 g, 4.7 mmol) was added. After stirring over night, the mixture was poured into water, acidified with 10% citric acid, and extracted with ethyl acetate. The organic extracts were washed with water and brine, dried over Na2SO4. After the condensation of the solvent, the residue was purified by flash column chromatography (SiO2, 1:1 hexane:ethyl aceate) to provide the title compound (1.7 g, 86%) as a light yellow solid.

Workup

  1. stirringAfter stirring over night
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customAfter the condensation of the solvent
  6. customthe residue was purified by flash column chromatography (SiO2, 1:1 hexane:ethyl aceate)

Sources & evidence

ORD record
ord-e76bcb9671b94d2f8b351024d4c0996a
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

Loading…