Pyridine → Toluene-4-thiosulfonic acid S-(7-tert-butyl-2,3-dioxo-1,2,3,4-tetrahydro-quinoxalin-6-yl)ester

HRID 23499Notes

Reaction equation

HRID 23499 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[SH:15])[NH:11][C:10](=[O:16])[C:9](=[O:17])[NH:8]2)([CH3:4])([CH3:3])[CH3:2].[S:18](Br)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19].N1C=CC=CC=1>CCOC(C)=O>[C:1]([C:5]1[CH:6]=[C:7]2[C:12]([NH:11][C:10](=[O:16])[C:9](=[O:17])[NH:8]2)=[CH:13][C:14]=1[S:15][S:18]([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 101308854-Methylbenzene-1-sulfonyl bromideHCID 225727956-tert-Butyl-7-mercapto-1,4-dihydro-quinoxaline-2,3-dione

Product 1

HCID 69735976Toluene-4-thiosulfonic acid S-(7-tert-butyl-2,3-dioxo-1,2,3,4-tetrahydro-quinoxalin-6-yl)ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared according to the General Method 15 using 6-tert-butyl-7-mercapto-1,4-dihydro-quinoxaline-2,3-dione (prepared in Example DDD, 9.1 mmol), tosyl bromide (2.1 g, 9.1 mmol), pyridine (2 mL), EtOAc (50 mL). The crude product was purified by flash silica gel chromatography (5%-10% MeOH in CH2Cl2) as eluents. MS(APCI): 405 (M+H).

Workup

  1. customThe crude product was purified by flash silica gel chromatography (5%-10% MeOH in CH2Cl2) as eluents

Sources & evidence

ORD record
ord-7ad3e437a0294e5ab25fa470060edb17
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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