Diisopropylethylamine → HCID 66788954, compound

HRID 641280Notes

Reaction equation

HRID 641280 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10][NH:9]2)=[O:5])[CH3:2].C(N(CC)C(C)C)(C)C.[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([O:43][CH3:44])=[C:37]([S:39](Cl)(=[O:41])=[O:40])[CH:38]=1>ClCCl.N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:11][CH2:10][N:9]2[S:39]([C:37]1[CH:38]=[C:33]([Cl:32])[CH:34]=[CH:35][C:36]=1[O:43][CH3:44])(=[O:40])=[O:41])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chlorideHCID 66789204HCID 66789204, compound

Product 1

HCID 66788954HCID 66788954, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

3,4-Dihydro-2H-quinoxaline-1,6-dicarboxylic acid 1-tert-butyl ester 6-ethyl ester (300 mg, 0.98 mmol) was dissolved in dichloromethane (20 mL) and pyridine (2 mL). N,N-Diisopropylethylamine (127 mg, 0.98 mmol) and 5-chloro-2-methoxy-benzensulfonyl chloride (300 mg, 1.24 mmol) were added, and the mixture was stirred at room temperature overnight. The solvent was evaporated, and the crude compound was purified by flash chromatography, yielding 4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-quinoxaline-1,6-dicarboxylic acid 1-tert-butyl ester 6-ethyl ester as a light yellow gum, 435 mg (87%), δH (300 MHz; CDCl3) 8.17 (1H, s), 8.05 (1H, s), 7.82 (1H, d), 7.74 (1H, d), 7.46 (1H, dd), 6.82 (1H, d), 4.35 (2H, q), 3.93 (2H, m), 3.71 (2H, m), 3.56 (3H, s), 1.48 (9H, s), 1.39 (3H, t).

Workup

  1. customThe solvent was evaporated
  2. customthe crude compound was purified by flash chromatography

Sources & evidence

ORD record
ord-76134d490bd0492d9d4c05d50328dad2
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

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