Water → HCID 53311107, compound

HRID 1967023Notes

Reaction equation

HRID 1967023 reaction equation
C[O:2][C:3](=[O:43])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:42])[C:12]2[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][C:21]=3[C:26]([N:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]([CH:38]4[CH2:40][CH2:39]4)[CH2:30][CH2:29]3)=[O:27])=[CH:14][C:13]=2[Cl:41])=[CH:6][CH:5]=1.O.O.[OH-].[Li+]>O1CCOCC1>[Cl:41][C:13]1[CH:14]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[C:26]([N:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]([CH:38]3[CH2:39][CH2:40]3)[CH2:30][CH2:29]2)=[O:27])[C:16]([Cl:18])=[CH:17][C:12]=1[C:11]([NH:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:43])=[O:2])=[CH:5][CH:6]=1)=[O:42]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 53311106HCID 53311106, compound

Product 1

HCID 53311107HCID 53311107, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.040 g (0.065 mmol) 4-{2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-benzoic acid methyl ester (Example 43) in 0.5 mL dioxane were added 0.5 mL water and 0.003 g (0.071 mmol) lithiumhydroxide monohydrate. The resulting suspension was stirred at room temperature for 2 h, followed by heating to 80° C. for 1 hour. The organic solvent was removed by evaporation and the pH of the resulting solution was adjusted to 1 to 2 using 1M aqueous hydrochloric acid. The suspension was stirred for 2 hours at room temperature, filtered and washed with water to yield the desired compound as a light brown solid (0.020 g, 51%). MS (ESI): m/z=603.12 [M+H]+.

Workup

  1. temperatureby heating to 80° C. for 1 hour
  2. customThe organic solvent was removed by evaporation
  3. stirringThe suspension was stirred for 2 hours at room temperature
  4. filtrationfiltered
  5. washwashed with water

Sources & evidence

ORD record
ord-4c06d0e0bfdc4e11ae0df8e3da4fb823
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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