Tetrahydrofuran → HCID 21101581, compound

HRID 1353410Notes

Reaction equation

HRID 1353410 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:22]3[CH2:27][CH2:26][N:25]([C:28]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)=[O:29])[CH2:24][CH2:23]3)=[CH:7][C:8]([NH:12][CH2:13][CH2:14][NH:15]C(C(F)(F)F)=O)=[N:9]2)=[CH:4][CH:3]=1.C1COCC1.[OH-].[K+]>CO>[NH2:15][CH2:14][CH2:13][NH:12][C:8]1[CH:7]=[C:6]([N:22]2[CH2:27][CH2:26][N:25]([C:28]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)=[O:29])[CH2:24][CH2:23]2)[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium Hydroxide2×HCID 21101792HCID 21101792, compound

Product 1

HCID 21101581HCID 21101581, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 7-Chloro-4-[4-(4-fluorphenylaminocarbonyl)piperazin-1-yl]-2-[2-(trifluoroacetamino)ethylamino]quinoline (13 mg, 0.024 mmol) was added THF (0.5 mL) and 0.5 N KOH (2.0 eq, 0.14 mL), the mixture was stirred at rt. for 2 h, additional 0.5 N KOH (0.5 mL, 10 eq.) was added and the reaction mixture was heated at 50° C. for 30 min, MeOH (0.2 ml) was added and heated at the same temperature for 30 min. Evaporation and dilution with AcOEt, washing with brine, usual workup gave the residue, which was purified by preparative TLC with 20% MeOH in DCM with 0.5% hydroxylamine by twice developing the plate to afford the title compound.

Workup

  1. temperaturethe reaction mixture was heated at 50° C. for 30 min
  2. temperatureheated at the same temperature for 30 min
  3. customEvaporation and dilution with AcOEt
  4. washwashing with brine, usual workup
  5. customgave the residue, which
  6. customwas purified by preparative TLC with 20% MeOH in DCM with 0.5% hydroxylamine

Sources & evidence

ORD record
ord-b3dde378920d48c8b307f758a7770efd
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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