Sodium Hydroxide → HCID 23593668, compound

HRID 433938Notes

Reaction equation

HRID 433938 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([NH:13][C:14]([NH:16][C:17]3[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([O:25]CC)=[O:24])=[C:19]([C:30]([F:33])([F:32])[F:31])[CH:18]=3)=[O:15])=[O:12])[CH:10]=[C:5]2[C:4]([CH3:34])=[N:3]1.[OH-].[Na+:36]>CN(C=O)C>[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([NH:13][C:14]([NH:16][C:17]3[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([O-:25])=[O:24])=[C:19]([C:30]([F:33])([F:32])[F:31])[CH:18]=3)=[O:15])=[O:12])[CH:10]=[C:5]2[C:4]([CH3:34])=[N:3]1.[Na+:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10277410HCID 10277410, compound

Product 1

HCID 23593668HCID 23593668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 2-[4-({[(1,3-dimethypyrazolo[5,4-b]pyridin-5-yl)carbonyl-amino]carbonyl}amino)-2-(trifluoromethyl)phenoxy]acetate (0.11 g) in DMF (3 mL) was treated with 5N sodium hydroxide solution (1.6 mL). The mixture was stirred at room temperature for 1.25 h, and then concentrated under reduced pressure. The residue was taken up in water (4 mL), filtered, and the filtrate was cooled in an ice-bath and acidified to pH 4 with concentrated hydrochloric acid. The precipitated solid was collected by filtration, washed with water, and dried under high vacuum. A portion of this material was suspended in water (5 mL) and treated with 5N sodium hydroxide solution (27 μL). The mixture was sonicated, filtered, and the filtrate lyophilized to yield the title compound. 1H NMR (DMSO-d6) δ 2.53 (s, 3H), 3.99 (s, 3H), 4.17 (s, 2H), 6.85 (d, J=8.8 Hz, 1H), 7.44-7.47 (br d, J=8.8 Hz, 1H), 8.03 (d, J=2.1 Hz, 1H), 8.52 (s, 1H) 8.79 (d, J=1.6 Hz, 1H), 9.23 (d, J=1.6 Hz, 1H), 11.50 (br s, 1H). MS (ESI) m/z 450.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationfiltered
  3. temperaturethe filtrate was cooled in an ice-bath
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried under high vacuum
  7. additiontreated with 5N sodium hydroxide solution (27 μL)
  8. customThe mixture was sonicated
  9. filtrationfiltered

Sources & evidence

ORD record
ord-5e78a5b67db849acb35b7b3d1bf23ff7
Source dataset
uspto-grants-2003_12
Patent number
US06670364B2

Reaction notes

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