Diisopropylethylamine → HCID 86718142, compound

HRID 2205154Notes

Reaction equation

HRID 2205154 reaction equation
[CH3:1][CH:2]([S:4](Cl)(=[O:6])=[O:5])[CH3:3].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:17][C:18]3[C:23]([N:24]=2)=[CH:22][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:20][CH:19]=3)=[CH:11][CH:10]=1.CCN(C(C)C)C(C)C>ClCCl>[C:29]1([C:16]2[C:15]([C:12]3[CH:13]=[CH:14][C:9]([NH:8][S:4]([CH:2]([CH3:3])[CH3:1])(=[O:6])=[O:5])=[CH:10][CH:11]=3)=[N:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=3)[N:17]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 824082-Propanesulfonyl chlorideHCID 86718143HCID 86718143, compound

Product 1

HCID 86718142HCID 86718142, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Propane-2-sulfonyl chloride (300 mg, 2.10 mmol, 5.00 equiv) was added to a solution of methyl 3-(4-aminophenyl)-2-phenylquinoxaline-6-carboxylate (150 mg, 0.42 mmol, 1.00 equiv) and DIEA (545 mg, 4.22 mmol, 10.00 equiv) in dichloromethane (30 mL) at 0° C., and the resulting solution was stirred overnight at room temperature. The reaction mixture was concentrated under vacuum and purified via silica gel column (ethyl acetate/petroleum ether (1:10)), affording 170 mg (87%) of methyl 2-phenyl-3-(4-(propan-2-ylsulfonamido)phenyl)quinoxaline-6-carboxylate as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified via silica gel column (ethyl acetate/petroleum ether (1:10))

Sources & evidence

ORD record
ord-a4fbb2952e54428f962ffd56d7c32f2c
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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