Sodium Hydroxide → HCID 178433648, compound

HRID 2271120Notes

Reaction equation

HRID 2271120 reaction equation
[OH-].[Na+].C([O:11][CH2:12][CH2:13][CH2:14][C:15]1[C:16]2[C:17]([C:22](=[O:32])[N:23]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[N:24]=2)=[CH:18][NH:19][C:20]=1[CH3:21])(=O)C1C=CC=CC=1>CO>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([N:23]2[C:22](=[O:32])[C:17]3=[CH:18][NH:19][C:20]([CH3:21])=[C:15]([CH2:14][CH2:13][CH2:12][OH:11])[C:16]3=[N:24]2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178433649HCID 178433649, compound

Product 1

HCID 178433648HCID 178433648, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium hydroxide (0.075 g, 1.88 mmol) in methanol (10 ml) was added the product of Example 105 (0.1 g, 0.42 mmol) and the mixture stirred for 18 hours. The solvent was evaporated in vacuo and the residue taken up in water and adjusted to pH 6 with 1N HCl. The yellow precipitate was extracted into 10% methanol/CH2Cl2 and the organic phase separated, dried, filtered and evaporated to give a yellow solid. Recrystallisation from MeOH/CH2Cl2/EtOAc afforded the title compound as a yellow solid (0.082 g, 60.5%). 1H NMR (360 MHz, DMSO-d6) δ12.22 (1H, br s), 8.44 (1H, s), 8.23 (2H, d, J 8.9 Hz), 7.46 (2H, d, J 8.9 Hz), 4.54 (1H, t, J 5.3 Hz), 3.44 (2H, dt, J 5.5, J 6.2 Hz), 2.71 (2H, t, J 7.2 Hz), 2.35 (3H, s), 1.78 (2H, t, J 7.2 Hz); MS (ES+) m/z 318/320 [MH]+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionThe yellow precipitate was extracted into 10% methanol/CH2Cl2
  3. customthe organic phase separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow solid
  8. customRecrystallisation from MeOH/CH2Cl2/EtOAc

Sources & evidence

ORD record
ord-3f8ce427d7d5457bb1abd3a36ffa9284
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

Loading…