Triethylamine → HCID 58583287, compound

HRID 1612361Notes

Reaction equation

HRID 1612361 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-7a43a8e6ace74718aefa1c804da83d42
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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