Sodium Hydroxide → HCID 66917791, compound

HRID 2235804Notes

Reaction equation

HRID 2235804 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([O:11][C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=3)[CH:7]=[CH:8][CH:9]=2)[C:4]([NH:22]CC(O)=O)=[N:3]1.[OH-].[Na+]>CCO.O>[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([O:11][C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=3)[CH:7]=[CH:8][CH:9]=2)[C:4]([NH2:22])=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11688828HCID 11688828, compound

Product 1

HCID 66917791HCID 66917791, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

[1-Methyl-4-(naphthalen-2-yloxy)-1H-indazol-3-ylamino]-acetic acid (A25) To a 50 mL round-bottomed, one-necked flask containing K-3 (90 mg, 0.25 mmol) was added 1:1 EtOH/H2O (2 mL). To this stirring suspension was added 15% aqueous NaOH (0.133 mL, 0.5 mmol) and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was concentrated on the vacuum line and the resulting solid was suspended in H2O (2 mL) and 1N HCl was added until a pH of 1-2 (litmus paper) was reached. The mixture was stirred at room temperature for 30 min and then filtered. The resulting solid was dried to afford 65 mg (75%) of A25 as an off-white solid. 1H NMR (400 MHz, DMSO-d6) 3.77 (s, 3H), 3.93 (s, 2H), 5.63 (br s, 1H), 6.18 (d, J=7.6 Hz, 1H), 7.07 (d, J=8.0 Hz, 1H), 7.18 (dd, J=8.0, 8.0 Hz, 1H), 7.41 (dd, J=8.8, 1.2 Hz, 1H), 7.51 (m, 2H), 7.63 (d, J=2.4 Hz, 1H), 7.89 (d, J=8.0 Hz, 1H), 7.96 (d, J=7.6 Hz, 1H), 8.02 (d, J=8.8 Hz, 1H), 12.45 (br s, 1H), LC/MS (86%) (ESI+) Calcd. for 347.4; Found: 348.7 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated on the vacuum line
  2. addition1N HCl was added until a pH of 1-2 (litmus paper)
  3. stirringThe mixture was stirred at room temperature for 30 min
  4. filtrationfiltered
  5. customThe resulting solid was dried
  6. customto afford 65 mg (75%) of A25 as an off-white solid

Sources & evidence

ORD record
ord-3f32506f32d34bd5b97a895a5bcdcbb5
Source dataset
uspto-grants-2010_05
Patent number
US07714017B2

Reaction notes

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