Diisopropylethylamine → HCID 178436914, compound

HRID 340020Notes

Reaction equation

HRID 340020 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Br.Br.Br.[CH2:38]([C:40]1[C:41]([C:48]2[CH:56]=[C:55]3[C:51]([C:52]([C:57]4[NH:58][C:59]5[CH2:64][CH2:63][NH:62][CH2:61][C:60]=5[N:65]=4)=[N:53][NH:54]3)=[CH:50][CH:49]=2)=[CH:42][C:43]([F:47])=[C:44]([OH:46])[CH:45]=1)[CH3:39].CCN(C(C)C)C(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:62]2[CH2:61][C:60]3[N:65]=[C:57]([C:52]4[C:51]5[C:55](=[CH:56][C:48]([C:41]6[CH:42]=[C:43]([F:47])[C:44]([OH:46])=[CH:45][C:40]=6[CH2:38][CH3:39])=[CH:49][CH:50]=5)[NH:54][N:53]=4)[NH:58][C:59]=3[CH2:64][CH2:63]2)=[O:10])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27628725-Chloro-2-picolinic acidHCID 1784192405-Ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazol[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt

Product 1

HCID 178436914HCID 178436914, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-pyridine-2-carboxylic acid (12 mg, 80 μmol) in DMF (1 mL) was added HBTU (32 mg, 85 μmol) and the resulting reaction mixture was stirred at room temperature for 30 minutes. 5-Ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt (Preparation 25, 50 mg, 80 μmol) and DIPEA (56 μL, 320 μmol) were added and stirring was continued at room temperature for 18 hours. Saturated aqueous sodium hydrogen carbonate solution (5 mL) was added to the reaction mixture. The resulting solid was collected by filtration and washed with further saturated aqueous sodium hydrogen carbonate solution. The crude material was purified by reverse phase chromatography (Method C) to afford 3.3 mg of the title compound.

Workup

  1. customthe resulting reaction mixture
  2. stirringstirring
  3. waitwas continued at room temperature for 18 hours
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with further saturated aqueous sodium hydrogen carbonate solution
  6. customThe crude material was purified by reverse phase chromatography (Method C)

Sources & evidence

ORD record
ord-57d0284c133047888dc38cdf59aba9b4
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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