Hydrochloric Acid → 2-(Azetidin-3-YL)-3-chloropyrazine hydrochloride

HRID 1850242Notes

Reaction equation

HRID 1850242 reaction equation
[Cl:1][C:2]1[C:3]([CH:8]2[CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.Cl>CO>[ClH:1].[NH:10]1[CH2:11][CH:8]([C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59351411Tert-butyl 3-(3-chloropyrazin-2-yl)azetidine-1-carboxylate

Product 1

HCID 717437842-(Azetidin-3-YL)-3-chloropyrazine hydrochlorideYield 200.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 3-(3-chloropyrazin-2-yl)azetidine-1-carboxylate (7) (300 g, 1.112 mol, 1 eq.) in methanol (6 L) was added concentrated HCl (400 mL, 4.8 mol, 4.3 eq.) and the resulting mixture was stirred at RT for 112 h. The mixture was concentrated and dried on rotavapor to obtain 230 g of 2-(azetidin-3-yl)-3-chloropyrazine hydrochloride (8).

Workup

  1. concentrationThe mixture was concentrated
  2. customdried on rotavapor

Sources & evidence

ORD record
ord-648299b147c14633895e512876776cdf
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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