Sodium Bicarbonate → HCID 22480127, compound

HRID 1353670Notes

Reaction equation

HRID 1353670 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:19]([C:21]4[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=4)=[O:20])[CH:16]=3)[N:11](C3CCCCO3)[N:10]=2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:19]([C:21]4[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=4)=[O:20])[CH:16]=3)[NH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22479702HCID 22479702, compound

Product 1

HCID 22480127HCID 22480127, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-{N-[3-(4-methoxyphenyl)-1-perhydro-2H-pyran-2-yl-1H-indazol-5-yl]carbamoyl}benzoate (0.099 g, 0.20 mmol) in anhydrous tetrahydrofuran (5 mL), 6.0N aqueous HCl was added (5 mL). The solution was stirred at room temperature for 48 hours. The reaction mixture was then neutralized with saturated aqueous sodium bicarbonate and the organic layer was extracted with ethyl acetate (10 mL, 3 times). The organic layer was dried over Na2SO4 and evaporated to dryness to afford the title compound (0.081 g, quantitative yield): ES-MS (m/z) 402 [M+1]+.

Workup

  1. extractionthe organic layer was extracted with ethyl acetate (10 mL, 3 times)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-4cf14939fe1f430aaf82e4a3606fa1a6
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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