N,N-Dimethylglycine → HCID 59485965, compound

HRID 1972253Notes

Reaction equation

HRID 1972253 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[CH2:11][O:10][C:9]2=[O:20])=[CH:4][CH:3]=1.Br[C:22]1[CH:27]=[N:26][CH:25]=[CH:24][N:23]=1.CN(C)CC(O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:22]4[CH:27]=[N:26][CH:25]=[CH:24][N:23]=4)[CH:14]=3)[CH2:11][O:10][C:9]2=[O:20])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 6428002-BromopyrazineHCID 59485707HCID 59485707, compound

Product 1

HCID 59485965HCID 59485965, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Reference: Org Lett 2003, 5(21), 3799. A small reaction tube fitted with a screw cap containing a septum is charged with (S)-3-(4-chlorophenyl)-4-(3-hydroxyphenyl)-oxazolidin-2-one (0.06 mmol), 2-bromopyrazine (0.076 mmol), CuI (0.04 mmol), N,N-dimethylglycine (0.04 mmol), Cs2CO3 (0.13 mmol) and 1,4-dioxane (1 mL) is stirred at 120° C. for 18 h. The reaction mixture is then cooled to room temperature and filtered through a Whatman 0.42 μM filter and purified by preparative HPLC (C-18, 10-90% ACN/water (0.05% TFA)). 1H NMR (CDCl3, 400 MHz) δ 8.41 (d, J=1.2 Hz, 1H), 8.29 (d, J=2.8 Hz, 1H), 8.04 (dd, J=2.8, 1.2 Hz, 1H), 7.43 (t, J=8.0 Hz, 1H), 7.34 (d, J=8.8 Hz, 2H), 7.24 (d, J=8.2 Hz, 2H), 7.12-7.19 (m, 2H), 7.10 (s, 1H), 5.37 (dd, J=8.8, 6.0 Hz, 1H), 4.80 (t, J=8.8 Hz, 1H), 4.26 (dd, J=8.8, 6.0 Hz, 1H); HPLC-MS calculated for C19H14ClN3O3 (M+H+) 368.1, found 368.1.

Workup

  1. customA small reaction tube fitted with a screw
  2. customcap
  3. additioncontaining a septum
  4. temperatureThe reaction mixture is then cooled to room temperature
  5. filtrationfiltered through a Whatman 0.42 μM
  6. filtrationfilter
  7. custompurified by preparative HPLC (C-18, 10-90% ACN/water (0.05% TFA))

Sources & evidence

ORD record
ord-706edb8e860a4a8c81f5ebbd6ea041d8
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

Loading…