Triethylamine → HCID 58583287, compound

HRID 1824276Notes

Reaction equation

HRID 1824276 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C(N(CC)CC)C.[CH2:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:18]([NH2:25])[C@H:17]1[OH:26]>CCCCO>[Cl:8][C:4]1[N:3]=[C:2]([NH:25][C@@H:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:16][C@@H:17]2[OH:26])[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 785042,6-DichloropyrazineHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanol

Product 1

HCID 58583287HCID 58583287, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 2,6-dichloropyrazine (5.0 g, 34 mmol) in n-BuOH (30 mL) was added triethylamine (6.8 g, 9.4 mL, 67 mmol) and (1R,2S)-(+)-cis-1-amino-2-indanol (5.0 g, 34 mmol). The mixture was heated at 115° C. overnight. The solution was cooled to rt and concentrated. Dissolve material in EtOAc (200 mL) and remove insoluble material by vacuum filtration. Wash filtrate sequentially with 4 N NaOH and sat. aq. NaCl. Dry organic extract over MgSO4, filter and concentrate. Purify by biotage MPLC (90 g column, 10% ethyl acetate/hexanes) to afford 4.85 g (57%) of (1R,2S)-1-[(6-chloropyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol as a solid: 1H NMR (CDCl3) δ 2.83–2.87, 3.08–3.13, 3.32, 4.54, 5.11, 5.28–5.31, 7.18–7.28, 7.73, 8.12; MS (ESI+) for C13H12ClN3O m/z 262 (M+H)+.

Workup

  1. temperatureThe solution was cooled to rt
  2. concentrationconcentrated
  3. customDissolve material in EtOAc (200 mL) and remove insoluble material
  4. filtrationby vacuum filtration
  5. extractionDry organic extract over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify by biotage MPLC (90 g column, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-06766ed653f74ac6a2f054822e34a5b8
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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