Potassium Carbonate → HCID 57185183, compound

HRID 1439945Notes

Reaction equation

HRID 1439945 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[F:16][C:17]([F:50])([F:49])[C:18]1[CH:19]=[C:20]([CH2:28][O:29][C@@H:30]2[CH2:35][CH2:34][CH2:33][N:32](CC3C=[NH+]C=CC=3)[C@@H:31]2[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1>CN(C)C=O.O>[F:26][C:24]([F:25])([F:27])[C:22]1[CH:21]=[C:20]([CH2:28][O:29][C@H:30]2[CH2:35][CH2:34][CH2:33][N:32]([CH2:2][C:3]3[CH:8]=[N:7][CH:6]=[CH:5][N:4]=3)[C@H:31]2[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:19]=[C:18]([C:17]([F:50])([F:16])[F:49])[CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 170169Pyrazine, 2-(chloromethyl)-HCID 131719281HCID 131719281, compound

Product 1

HCID 57185183HCID 57185183, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-(Chloromethyl)pyrazine (0.17 g), potassium carbonate (0.6 g) and the compound of Description 3 (0.35 g) were suspended in dimethylformamide (3 ml); the reaction mixture was heated at 60° C. for 12 h. The mixture was cooled, diluted with water (30 ml) and extracted with ethyl acetate (2×20 ml). The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo to afford a brown oil. The product was purified by column chromatography on silica gel using a gradient elution of 15-35% ethyl acetate in hexane. This afforded the product as a white solid, which was recrystallised from pentane to give colourless crystals: mp 108°-110° C. 1H NMR (360 MHz, DMSO-d6) d 1.42-1.60 (2H, m NCH2CH2CH2), 1.77-1.92 (1H, m, NCH2CHH), 2.13-2.25 (2H, m, NCHH+NCH2CHH), 2.84-2.92 (1H, m, NCHH), 3.12 (1H, d, J=14.0 Hz, NCHH-pyrazine), 3.55 (1H, m, CHO), 3.63 (1H, m, CHPh), 3.78 (1H, d, 14.0 Hz, NCHH-pyrazine), 4.11 (1H, d, J=13.0 Hz, OCHHAr), 4.64 (1H, d, J=13.0 Hz, OCHHAr), 7.20-7.33 (3H, m, ArH), 7.49-7.56 (2H, m, ArH), 7.71 (2H, s, ArH), 7.93 (1H, s, ArH), 8.48-8.63 (3H, m, ArH); MS (CI+) 496 (M+ +1, 60%). Found: C, 60.90; H, 4.86; N, 8.48. Calcd. for C25H23F6N3O: C, 60.60; H, 4.68; N, 8.48%.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto afford a brown oil
  7. customThe product was purified by column chromatography on silica gel using
  8. washa gradient elution of 15-35% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0a91958508e24181b903c310f9b3eaa9
Source dataset
uspto-grants-1996_03
Patent number
US05496833

Reaction notes

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