1,4-Dioxane hydrochloride → 3-(4-(Azetidin-3-yl)phenylamino)-5-bromo-1-methylpyrazin-2(1H)-one Hydrochloride

HRID 1919098Notes

Reaction equation

HRID 1919098 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]3)=[CH:11][CH:10]=2)[C:5](=[O:26])[N:4]([CH3:27])[CH:3]=1.[ClH:28].O1CCOCC1>CO>[ClH:28].[NH:17]1[CH2:18][CH:15]([C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6]3[C:5](=[O:26])[N:4]([CH3:27])[CH:3]=[C:2]([Br:1])[N:7]=3)=[CH:14][CH:13]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 58044293tert-Butyl 3-(4-(6-Bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)phenyl)azetidine-1-carboxylate

Product 1

HCID 866612603-(4-(Azetidin-3-yl)phenylamino)-5-bromo-1-methylpyrazin-2(1H)-one HydrochlorideYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 298b (690 mg, 1.6 mmol) and HCl/1,4-dioxane (8M, 8 mL) in methanol (30 mL) was stirred at room temperature overnight. The mixture was evaporated in vacuo and the residue was purified on reverse phase Combi-flash to give 298c (100 mg, 17%). MS: [M+H]+ 335.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified on reverse phase Combi-flash

Sources & evidence

ORD record
ord-dd84b521ecd34ecda81fe15746dd0636
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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