Benzocaine → HCID 66788528, compound

HRID 1660800Notes

Reaction equation

HRID 1660800 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18](O)=[O:19])=[CH:15][CH:16]=2)[N:11]([S:21]([C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=2[O:31][CH3:32])(=[O:23])=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.N1C(Cl)=NC(Cl)=NC=1Cl.[CH2:49]([O:51][C:52](=[O:60])[C:53]1[CH:58]=[CH:57][C:56]([NH2:59])=[CH:55][CH:54]=1)[CH3:50]>CC(C)=O.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18](=[O:19])[NH:59][C:56]3[CH:57]=[CH:58][C:53]([C:52]([O:51][CH2:49][CH3:50])=[O:60])=[CH:54][CH:55]=3)=[CH:15][CH:16]=2)[N:11]([S:21]([C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=2[O:31][CH3:32])(=[O:23])=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 2337BenzocaineHCID 7954Cyanuric chlorideHCID 8471Triethylamine2×HCID 66788889HCID 66788889, compound

Product 1

HCID 66788528HCID 66788528, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-quinoxaline-1,6-dicarboxylic acid 1-tert-butyl ester (100 mg, 0.21 mmol) in acetone (30 mL) and tetrahydrofuran (10 mL) was treated with triethylamine (21 mg, 0.21 mmol) and stirred at room temperature 1 hour. A solution of cyanuric chloride (46 mg, 0.25 mmol) in tetrahydrofurane (2 mL) was added dropwise over a period of 1 hour. The reaction mixture was stirred at room temperature for 2 hours, then 4-amino-benzoic acid ethyl ester (51 mg, 0.31 mmol) and a further aliquot of triethylamine (42 mg, 0.42 mmol) were added. The reaction mixture was stirred at room temperature for 48 hours, the solvents were then removed. The residue was purified by flash chromatography, to yield 4-(5-chloro-2-methoxy-benzenesulfonyl)-6-(4-ethoxycarbonyl-phenylcarbamoyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester as a light yellow solid, 100 mg (77%), δH (300 MHz; CDCl3) 8.01-8.08 (4H, m), 7.94 (1H, d), 7.73-7.77 (3H, m), 7.48 (1H, dd), 6.82 (1H, d), 4.38 (2H, q), 3.89 (2H, m), 3.64 (2H, m), 3.47 (3H, s), 1.48 (9H, s), 1.40 (3H, t).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. stirringThe reaction mixture was stirred at room temperature for 48 hours
  3. customthe solvents were then removed
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1f61fb46dbf14ebfbcb267230a26159a
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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