N-bromobutanimide → methyl 3-bromo-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate

HRID 1612362Notes

Reaction equation

HRID 1612362 reaction equation
[OH:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12]1[N:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[N:14][CH:13]=1.[Br:22]N1C(=O)CCC1=O>C(Cl)Cl>[Br:22][C:15]1[C:16]([C:18]([O:20][CH3:21])=[O:19])=[N:17][C:12]([NH:11][C@@H:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:10][C@@H:2]2[OH:1])=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58583396Methyl 6-{[(1r,2s)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino}pyrazine-2-carboxylate

Product 1

HCID 58583440methyl 3-bromo-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylateYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate (1.0 g, 3.5 mmol) in CH2Cl2 (35 mL) was added N-bromsuccinimide (0.69 g, 3.86 mmol). Stir at t for 2 hr. Wash the reaction with sat. aq. NaHCO3. The organic extract was dried over MgSO4, filtered and concentrated. Purify by biotage MPLC (90 g column, 20% ethyl acetate/hexanes) to afford 380 mg (30%) of methyl 3-bromo-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate as a solid: 1H NMR (CDCl3) δ 3.01-3.06, 3.24-3.29, 4.00, 4.75-4.78, 5.45-5.46, 7.25-7.32, 7.94; MS (ESI+) for C15H14BrN3O3 m/z 386 (M+H)+.

Workup

  1. washWash
  2. customthe reaction with sat. aq. NaHCO3
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurify by biotage MPLC (90 g column, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b4e44fff478c46b7a742a8906373fd99
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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