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HRID525339

反应详情

EQUATION

反应方程式

HRID 525339 的结构方程式

REACTANTS

反应物

4
结构：CNCCNC
HCID8070

N,N'-Dimethylethane-1,2-diamine

C4H12N2

结构：O=C([O-])[O-].[K+].[K+]
HCID11430

Potassium Carbonate

CK2O3

结构：O=c1[nH]c2ccncc2[nH]1
HCID11686916

未命名化合物

结构：CC1(C)OC(=O)N(c2ccc(Br)cc2)[C@H]1c1ccccc1
HCID89814002

未命名化合物

PRODUCTS

生成物

2
结构：CC1(C)OC(=O)N(c2ccc(-n3c(=O)[nH]c4cnccc43)cc2)[C@H]1c1ccccc1
HCID89815772

未命名化合物

收率 4%
结构：CC1(C)OC(=O)N(c2ccc(-n3c(=O)[nH]c4ccncc43)cc2)[C@H]1c1ccccc1
HCID89827457

未命名化合物

收率 4%

AUXILIARIES

试剂、催化剂与溶剂

3
结构：[Cu][I]
催化剂HCID24350

Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)

CuI

结构：CCCCO
溶剂HCID263

1-Butanol

C4H10O

结构：CO.O
溶剂HCID22242641

Methanol--water (1/1)

CH6O2

CONDITIONS

反应条件

温度
110 °C

PROCEDURE

实验过程

To a vial charged with (S)-3-(4-bromophenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.100 mg, 0.289 μmol), potassium carbonate (0.120 mg, 0.867 mol), copper (I) iodide (0.055 mg, 0.289 μmol), and 1H-imidazo[4,5-c]pyridin-2(3H)-one (commercially available from Prime Organics Inc. Woburn, Mass.) (117 mg, 0.867 μmol) were added n-butanol (1.155 μL) and N1,N2-dimethylethane-1,2-diamine (0.051 mg, 0.578 μmol). The suspension was purged with nitrogen, and then sealed and shaken overnight at 110° C. The resulting suspension was cooled to room temperature and filtered through Celite® brand filter aid. The filtrate was dried under reduced pressure and the residue was dissolved in DMSO and purified using RP-HPLC ramping ACN in H2O (10-90%, 0.1% TFA throughout). Separation of isomers was accomplished and the respective product containing eluents were dried under reduced pressure providing products which were lyophilized from MeOH/H2O providing (S)-5,5-dimethyl-3-(4-(2-oxo-1H-imidazo[4,5-c]pyridin-3(2H)-yl)phenyl)-4-phenyloxazolidin-2-one (5 mg, 4%) as a yellow solid and (S)-5,5-dimethyl-3-(4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)phenyl)-4-phenyloxazolidin-2-one (5 mg, 4%) as a light brown solid. Structures were assigned arbitrarily. Data for product A: 1H NMR (500 MHz, DMSO-d6) δ=8.22 (d, J=5.2 Hz, 1H), 8.14 (s, 1H), 7.69-7.64 (m, 2H), 7.51 (d, J=9.0 Hz, 2H), 7.42-7.38 (m, 2H), 7.35-7.28 (m, 3H), 7.12 (d, J=5.2 Hz, 1H), 5.51 (s, 1H), 1.66 (s, 3H), 0.93 (s, 3H). m/z (ESI) 401.2 (M+H)+. Data for product B: 1H NMR (500 MHz, DMSO-d6) δ=8.29 (s, 1H), 8.18 (s, 1H), 7.67 (d, J=9.0 Hz, 2H), 7.47 (d, J=8.9 Hz, 2H), 7.42-7.38 (m, 2H), 7.35-7.28 (m, 3H), 6.99 (d, J=5.4 Hz, 1H), 5.51 (s, 1H), 1.66 (s, 3H), 0.93 (s, 3H). m/z (ESI) 401.2 (M+H)+.

WORKUP

后处理

  1. customThe suspension was purged with nitrogen
  2. customsealed
  3. temperatureThe resulting suspension was cooled to room temperature
  4. filtrationfiltered through Celite® brand
  5. filtrationfilter aid
  6. customThe filtrate was dried under reduced pressure
  7. dissolutionthe residue was dissolved in DMSO
  8. custompurified
  9. customSeparation of isomers
  10. additionthe respective product containing eluents
  11. customwere dried under reduced pressure
  12. customproviding products which