Potassium Hydroxide → HCID 59252135, compound

HRID 658502Notes

Reaction equation

HRID 658502 reaction equation
CN[C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19]([NH:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([CH3:31])[N:26]=[CH:25]4)=[O:20])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].[OH-:32].[K+]>CO.O>[CH3:31][N:27]1[C:28]2[C:24](=[CH:23][C:22]([NH:21][C:19]([NH:18][C:14]3[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=3)[O:11][C:9]3[CH:8]=[CH:7][N:6]=[C:5]([C:3]([OH:32])=[O:4])[CH:10]=3)=[O:20])=[CH:30][CH:29]=2)[CH:25]=[N:26]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10454569HCID 10454569, compound

Product 1

HCID 59252135HCID 59252135, compoundYield 717.6%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

A mixture of N-methyl-4-[3-({[(1-methyl-1H-indazol-5-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide (80 mg, 0.19 mmol) and powdered potassium hydroxide (0.03 g, 0.56 mmol) was dissolved in MeOH/H2O (4 mL, 3:1), and the reaction mixture was heated at 40° C. for 3 h. The solvent was removed in vacuo, the crude residue dissolved in H2O (5 mL), and precipitated on being neutralized with aq. 1N HCl. The precipitated solid was washed with water and then CH2Cl2 to give 0.55 g (70%) of the carboxylic acid. 1H-NMR (DMSO-d6) δ 9.97 (s, 1H), 9.77 (s, 1H), 8.46 (d, 1H), 7.93 (s, 1H), 7.90 (s, 1H), 7.51 (d, 1H), 7.43-7.34 (m, 5H), 7.07 (dd, 1H), 6.73 (dd, 1H), 3.97 (s, 3H); MS LC-MS (M+H)+=404.1, RT=2.45 min.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe crude residue dissolved in H2O (5 mL)
  3. customprecipitated
  4. washThe precipitated solid was washed with water

Sources & evidence

ORD record
ord-928af233fbb843789d7d49440fab3c65
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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