Hydrochloric Acid → HCID 22136534, compound

HRID 1827454Notes

Reaction equation

HRID 1827454 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([O:23][CH3:24])=[O:22])=[CH:11][CH:12]=2)[N:7]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[N:6]=1)=[O:4].[OH-].[Na+].Cl>CO.O1CCCC1.O.CCOC(C)=O>[CH3:24][O:23][C:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([C:3]([OH:4])=[O:2])=[N:6][N:7]2[CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)=[CH:12][CH:11]=1)=[O:22]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23577862HCID 23577862, compound

Product 1

HCID 22136534HCID 22136534, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(2-Methoxycarbonyl-phenylamino)-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboxylic acid methyl ester (2.05 g, 5 mmol) in methanol (18 mL) and tetrahydrofuran (8 mL), was added a solution of sodium hydroxide (0.30 g, 7.5 mmol) in water (2.7 mL). The reaction was stirred at room temperature for 3 hours and was then neutralized with 1 N HCl to a pH of 1. The mixture was diluted with EtOAc (25 mL) and water (25 mL). After separating the layers, the aqueous layer was washed with CH2Cl2 (3×25 mL). The combined organic extracts were washed with saturated NaCl (100 mL) and then dried over Na2SO4. The solids were filtered and the liquid was concentrated to an oil. The product was crystallized from EtOAc and Hexanes to yield the desired product (1.616 g, 82%).

Workup

  1. customAfter separating the layers
  2. washthe aqueous layer was washed with CH2Cl2 (3×25 mL)
  3. washThe combined organic extracts were washed with saturated NaCl (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solids were filtered
  6. concentrationthe liquid was concentrated to an oil
  7. customThe product was crystallized from EtOAc and Hexanes

Sources & evidence

ORD record
ord-66e3b4573ec241d9b41fefe6f6bbcece
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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