Sodium Hydroxide → HCID 24762549, compound

HRID 1660802Notes

Reaction equation

HRID 1660802 reaction equation
C([O:3][C:4](=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH2:19][CH2:18][N:17]3[S:24]([C:27]2[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=2[O:34][CH3:35])(=[O:26])=[O:25])=[O:13])=[CH:7][CH:6]=1)C.[OH-].[Na+]>O1CCCC1.CO>[Cl:33][C:31]1[CH:30]=[CH:29][C:28]([O:34][CH3:35])=[C:27]([S:24]([N:17]2[C:16]3[C:21](=[CH:22][CH:23]=[C:14]([C:12]([NH:11][C:8]4[CH:9]=[CH:10][C:5]([C:4]([OH:36])=[O:3])=[CH:6][CH:7]=4)=[O:13])[CH:15]=3)[NH:20][CH2:19][CH2:18]2)(=[O:26])=[O:25])[CH:32]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66789450HCID 66789450, compound

Product 1

HCID 24762549HCID 24762549, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-{[4-(5-chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoxaline-6-carbonyl]-amino}-benzoic acid ethyl ester (30 mg, 0.06 mmol) in tetrahydrofuran (2 mL) and methanol (2 mL) was treated with NaOH 2N (2 mL) and warmed until a clear solution was obtained. The mixture was stirred at room temperature 2 hours, the organic solvents were then partially removed. The aqueous slurry was acidified with HCl 1N (4 mL) and the resulting precipitate filtered, washing with water. 4-{[4-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoxaline-6-carbonyl]-amino}-benzoic acid was obtained as a white solid, 26 mg (91%), MS (ISP): m/e=499.9, 501.9 (M−H); δH (300 MHz; d6-DMSO) 12.67 (1H, s), 10.15 (1H, s), 7.91 (4H, s), 7.89 (1H, s), 7.81 (1H, s), 7.73 (1H, d), 7.63 (1H, d), 7.23 (1H, d), 6.88 (1H, bs), 6.66 (1H, d), 3.64 (2H, bs), 3.53 (3H, s), 2.99 (2H, bs).

Workup

  1. temperaturewarmed until a clear solution
  2. customwas obtained
  3. customthe organic solvents were then partially removed
  4. filtrationthe resulting precipitate filtered
  5. washwashing with water

Sources & evidence

ORD record
ord-a8dd636fadf24340a2fad4f62ed093f2
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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