2,6-Dichlorobenzoyl chloride → 2,6-dichloro-N-[4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-benzamide

HRID 1054917Notes

Reaction equation

HRID 1054917 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([N:10]2[CH2:15][CH2:14][O:13][C:12]3[CH:16]=[CH:17][C:18]([NH2:20])=[N:19][C:11]2=3)(=[O:9])=[O:8])[CH:2]=1.[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:24]=1[C:25](Cl)=[O:26].C([O-])(O)=O.[Na+]>O1CCOCC1.O>[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:24]=1[C:25]([NH:20][C:18]1[CH:17]=[CH:16][C:12]2[O:13][CH2:14][CH2:15][N:10]([S:7]([C:3]3[CH:2]=[C:1]([CH3:21])[CH:6]=[CH:5][CH:4]=3)(=[O:9])=[O:8])[C:11]=2[N:19]=1)=[O:26]

Participants

6

Reactant 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 1180617154-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-ylamine

Product 1

HCID 725442132,6-dichloro-N-[4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4-(Toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-ylamine (20 mg, 0.065 mmol) was dissolved in p-dioxane (0.400 mL) and water (0.100 mL), followed by 2,6-dichlorobenzoyl chloride (21 μL, 0.098 mmol) and NaHCO3 (11 mg, 0.13 mmol). The resulting mixture was stirred at room temperature for 15 hours, concentrated under vacuum, and purified by HPLC to give 2,6-dichloro-N-[4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-benzamide. LCMS (ESI): calc. C21H17Cl2N3O4S=477; obs. M+H=478.

Workup

  1. concentrationconcentrated under vacuum
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-f749c899269a454cb124f1023137a824
Source dataset
uspto-grants-2016_07
Patent number
US09394315B2

Reaction notes

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