Water → HCID 178496564, compound

HRID 1047231Notes

Reaction equation

HRID 1047231 reaction equation
Br[C:2]1[C:3]([NH:9][CH2:10][C:11]([O:13]CC)=O)=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[CH3:16][O:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([CH2:24][NH2:25])[CH2:20][CH2:19]1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[Br:8][C:6]1[N:7]=[C:2]2[N:25]([CH2:24][C@H:21]3[CH2:22][CH2:23][C@H:18]([O:17][CH3:16])[CH2:19][CH2:20]3)[C:11](=[O:13])[CH2:10][NH:9][C:3]2=[N:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 57550751Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetateHCID 178496570HCID 178496570, compound

Product 1

HCID 178496564HCID 178496564, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A solution of ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate (500 mg, 1.47 mmol), ((trans)-4-methoxycyclohexyl)methanamine (317 mg, 2.21 mmol) and diisopropylethyl amine (0.77 mL, 4.42 mmol) in anhydrous dimethylsulfoxide (8.0 mL) was placed in a microwave vessel (20 mL). The reaction was heated to 150° C. for 1 h. The reaction was poured into water, extracted with ethyl acetate (2×100 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting material was dissolved in acetic acid (30 mL) and placed in a sealed tube. The reaction was heated to 120° C. overnight. The solution was cooled, concentrated under reduced pressure, neutralized with saturated sodium bicarbonate, extracted with ethyl acetate (3×100 mL), dried over sodium sulfate, filtered and adsorbed onto silica gel. Purification by flash chromatography (50% ethyl acetate in hexanes) gave a light orange solid (400 mg, 1.12 mmol, 76% yield). MS (ESI) m/z 355.2 [M+]+, 357.2 {M+2]+.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting material was dissolved in acetic acid (30 mL)
  6. customplaced in a sealed tube
  7. temperatureThe reaction was heated to 120° C. overnight
  8. temperatureThe solution was cooled
  9. concentrationconcentrated under reduced pressure
  10. extractionextracted with ethyl acetate (3×100 mL)
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. customPurification by flash chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ebe8ada62f164d9f9e0cb7810bbfb148
Source dataset
uspto-grants-2013_10
Patent number
US08569494B2

Reaction notes

Loading…