Acetic Acid → HCID 178436906, compound

HRID 340027Notes

Reaction equation

HRID 340027 reaction equation
Br.Br.Br.[CH2:4]([C:6]1[C:7]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([C:23]4[NH:24][C:25]5[CH2:30][CH2:29][NH:28][CH2:27][C:26]=5[N:31]=4)=[N:19][NH:20]3)=[CH:16][CH:15]=2)=[CH:8][C:9]([F:13])=[C:10]([OH:12])[CH:11]=1)[CH3:5].[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH:37]=O.CCN(C(C)C)C(C)C.C[C:52]([OH:54])=[O:53].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH:52]([OH:54])=[O:53].[CH2:4]([C:6]1[C:7]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([C:23]4[NH:24][C:25]5[CH2:30][CH2:29][N:28]([CH2:37][C:36]6[CH:39]=[CH:40][CH:41]=[C:34]([O:33][CH3:32])[CH:35]=6)[CH2:27][C:26]=5[N:31]=4)=[N:19][NH:20]3)=[CH:16][CH:15]=2)=[CH:8][C:9]([F:13])=[C:10]([OH:12])[CH:11]=1)[CH3:5]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 115693-MethoxybenzaldehydeHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 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 178436906HCID 178436906, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 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, 132 μmol) in DMF (1 mL), was added 3-methoxy-benzaldehyde (27 mg, 198 μmol), DIPEA (34 mg, 46 μL, 264 μmol) and AcOH (11.8 mg, 11 μL, 198 μmol). The reaction mixture was stirred at room temperature for 1 hour. STAB (42 mg, 198 μmol) was added and stirring was continued 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 30.1 mg of the title compound.

Workup

  1. additionSTAB (42 mg, 198 μmol) was added
  2. stirringstirring
  3. waitwas continued 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-e53a78bfe9734f079a5a9f792e0920a2
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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