Sodium Bicarbonate → N-(5-(7-((4-oxaspiro[2.4]heptane-6-yl)aminopropoxy)quinolin-4-yloxy)pyridin-2-yl)-2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxamide

HRID 1969404Notes

Reaction equation

HRID 1969404 reaction equation
[CH2:1]1[C:3]2([CH2:7][CH:6]([N:8]([CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:29]=[C:28]4[C:23]([C:24]([O:30][C:31]5[CH:32]=[CH:33][C:34]([NH:37][C:38]([C:40]6[C:41](=[O:53])[N:42]([C:47]7[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=7)[N:43]([CH3:46])[C:44]=6[CH3:45])=[O:39])=[N:35][CH:36]=5)=[CH:25][CH:26]=[N:27]4)=[CH:22][CH:21]=3)C(OC(C)(C)C)=O)[CH2:5][O:4]2)[CH2:2]1.Cl.C1COCC1.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:2]1[C:3]2([CH2:7][CH:6]([NH:8][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:29]=[C:28]4[C:23]([C:24]([O:30][C:31]5[CH:32]=[CH:33][C:34]([NH:37][C:38]([C:40]6[C:41](=[O:53])[N:42]([C:47]7[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=7)[N:43]([CH3:46])[C:44]=6[CH3:45])=[O:39])=[N:35][CH:36]=5)=[CH:25][CH:26]=[N:27]4)=[CH:22][CH:21]=3)[CH2:5][O:4]2)[CH2:1]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18422008HCl tetrahydrofuranHCID 59278578HCID 59278578, compound

Product 1

HCID 46202280N-(5-(7-((4-oxaspiro[2.4]heptane-6-yl)aminopropoxy)quinolin-4-yloxy)pyridin-2-yl)-2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-(7-((N-(4-oxaspiro[2.4]heptane-6-yl)-tert butoxycarbonylamino)propoxy)quinolin-4-yloxy)pyridin-2-yl)-2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxamide (50 mg, 0.069 mmol) in dry THF (2 mL) was added 2 M HCl/THF (8 mmol). After stirring at room temperature for 4 hrs, 10 mL of saturated NaHCO3 aqueous solution was added to quench the reaction. The mixture was extracted with EtOAc (15 mL×2). The combined organic phases were dried over Na2SO4, concentrated in vacuo. The crude product was chromatographed with a silica gel column (5:1 (v/v) EtOAc/MeOH) to give the title compound as a white solid (30 mg, 69%).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with EtOAc (15 mL×2)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was chromatographed with a silica gel column (5:1 (v/v) EtOAc/MeOH)

Sources & evidence

ORD record
ord-a3a65c7849414275bd4a6ba06b9d1c66
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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