Diisopropylethylamine → HCID 178436937, compound

HRID 2038669Notes

Reaction equation

HRID 2038669 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Br.Br.Br.[CH2:45]([C:47]1[C:48]([C:55]2[CH:63]=[C:62]3[C:58]([C:59]([C:64]4[NH:65][C:66]5[CH2:71][CH2:70][NH:69][CH2:68][C:67]=5[N:72]=4)=[N:60][NH:61]3)=[CH:57][CH:56]=2)=[CH:49][C:50]([F:54])=[C:51]([OH:53])[CH:52]=1)[CH3:46].CCN(C(C)C)C(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:45]([C:47]1[CH:52]=[C:51]([OH:53])[C:50]([F:54])=[CH:49][C:48]=1[C:55]1[CH:63]=[C:62]2[C:58]([C:59]([C:64]3[NH:65][C:66]4[CH2:71][CH2:70][N:69]([C:11]([C:8]5[CH:7]=[N:6][C:5]([O:4][C:3]6[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=6[F:1])=[CH:10][N:9]=5)=[O:13])[CH2:68][C:67]=4[N:72]=3)=[N:60][NH:61]2)=[CH:57][CH:56]=1)[CH3:46]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 463182515-(2-Fluorophenoxy)-2-pyrazinecarboxylic 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 178436937HCID 178436937, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2-fluoro-phenoxy)-pyrazine-2-carboxylic acid (Preparation 45, 19 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 HPLC Method B to afford 8.3 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 HPLC Method B

Sources & evidence

ORD record
ord-812291c2bb3d4c5b92a9fc60e4035838
Source dataset
uspto-grants-2013_11
Patent number
US08575336B2

Reaction notes

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