Sodium Hydroxide → 1-(1-methylethyl)-6-(4-morpholinylsulfonyl)-1H-indazole-4-carboxylic acid

HRID 1476478Notes

Reaction equation

HRID 1476478 reaction equation
[OH-].[Na+].[CH3:3][CH:4]([N:6]1[C:14]2[CH:13]=[C:12]([S:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)(=[O:17])=[O:16])[CH:11]=[C:10]([C:24]([O:26]C)=[O:25])[C:9]=2[CH:8]=[N:7]1)[CH3:5]>C(O)C>[CH3:5][CH:4]([N:6]1[C:14]2[CH:13]=[C:12]([S:15]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)(=[O:16])=[O:17])[CH:11]=[C:10]([C:24]([OH:26])=[O:25])[C:9]=2[CH:8]=[N:7]1)[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68210332HCID 68210332, compound

Product 1

HCID 674681771-(1-methylethyl)-6-(4-morpholinylsulfonyl)-1H-indazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (0.980 mL, 0.980 mmol) was added to a solution of methyl 1-(1-methylethyl)-6-(4-morpholinylsulfonyl)-1H-indazole-4-carboxylate (90 mg, 0.245 mmol) in ethanol (30 mL) and heated at reflux for 1 hour. The solvent was removed in vacuo and the residue suspended in water (20 mL). The contents were acidified by addition of acetic acid, and extracted with DCM (4×30 mL). The combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The product was collected as 90 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.63-1.78 (m, 6H), 3.02-3.24 (m, 4H), 3.67-3.88 (m, 4H), 5.00 (dt, J=13.20, 6.66 Hz, 1H), 8.21 (s, 1H), 8.31 (s, 1H), 8.71 (s, 1H), LCMS (ES) [M+H]+ 354.2

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customThe solvent was removed in vacuo
  4. additionThe contents were acidified by addition of acetic acid
  5. extractionextracted with DCM (4×30 mL)
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe product was collected as 90 mg

Sources & evidence

ORD record
ord-a39e1608fd574defad7cfa782ac275e9
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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