Water → HCID 59352988, compound

HRID 1914724Notes

Reaction equation

HRID 1914724 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[NH:12][C:13]1[C:22]([NH:23][S:24]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)(=[O:26])=[O:25])=[N:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.C([O-])([O-])=O.[K+].[K+].O>CO>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:33])=[O:2])=[C:5]([NH:12][C:13]2[C:22]([NH:23][S:24]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)(=[O:25])=[O:26])=[N:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 24992461HCID 24992461, compound

Product 1

HCID 59352988HCID 59352988, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl-4-methoxy-2-({3-[(pyridin-3-ylsulfonyl)amino]quinoxalin-2-yl}amino)benzoate (2200 mg; 4.73 mmol; 1 eq) and K2CO3 (8.5 g; 61.44 mmol; 13 eq) are taken up in MeOH (100 mL) and water (25 mL) and heated up to 60° C. overnight. The reaction mixture is concentrated to half the volume and some black residue is removed by filtration. The clear solution is neutralised with aqueous citric acid 10%. After 1 h at 4° C., the precipitate formed is filtered off and washed with water. After drying under vacuum at 40° C. overnight, it affords 2.01 g (94%) of the title compound as a yellow powder. 1H NMR (DMSO-d6) δ 13.17 (s, 1H), 12.49 (br s, 1H), 12.27 (s, 1H), 9.25 (d, J=1.9 Hz, 1H), 9.08 (d, J=2.6 Hz, 1H), 8.81-8.79 (m, 1H), 8.47-8.43 (m, 1H), 7.98 (d, J=9.0 Hz, 1H), 7.93 (br s, 1H), 7.68-7.60 (m, 2H), 7.44-7.40 (m, 2H), 6.70 (dd, J=8.7, 2.6 Hz, 1H), 3.91 (s, 3H). HPLC (max plot) 99%; Rt 4.04 min. LC/MS: (ES+): 452.3, (ES−): 450.3.

Workup

  1. concentrationThe reaction mixture is concentrated to half the volume
  2. customsome black residue is removed by filtration
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washwashed with water
  6. customAfter drying under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-527c12bebfb7497bb9f21cb21bfdc0fe
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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