Diisopropylethylamine → HCID 66788954, compound

HRID 1360248Notes

Reaction equation

HRID 1360248 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-benzenesulfonyl 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%), H (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-365a770abbe64dcd99834b2b6f1a87e5
Source dataset
uspto-grants-2011_02
Patent number
US07879845B2

Reaction notes

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