Water → HCID 19784181, compound

HRID 256880Notes

Reaction equation

HRID 256880 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9]([CH:13]1[CH:18]2[CH2:19][N:15]([CH2:16][C:17]2([O:22][CH3:23])[O:20][CH3:21])[CH2:14]1)([O:11][CH3:12])=[O:10].I[C:25]1[CH:30]=[N:29][CH:28]=[CH:27][N:26]=1.O>C1COCC1.ClCCl>[N:26]1[CH:27]=[CH:28][N:29]=[CH:30][C:25]=1[C:13]1([C:9]([O:11][CH3:12])=[O:10])[CH:18]2[CH2:19][N:15]([CH2:16][C:17]2([O:20][CH3:21])[O:22][CH3:23])[CH2:14]1

Participants

7

Reactant 4

HCID 962WaterHCID 642841IodopyrazineHCID 2724682Lithium diisopropylamideHCID 20079405HCID 20079405, compound

Product 1

HCID 19784181HCID 19784181, compoundYield 7.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Lithium diisopropylamide (3.7 ml of a 1.5M solution in THF, 5.58 mmol) was added dropwise to a solution of 3-carbomethoxy-5,5-dimethoxy-1-azabicyclo[2.2.1]heptane (1 g, 4.7 mmol) in THF (40 ml), at -78° C., and stirred for 2 h. A solution of 2-iodopyrazine (1.15 g, 5.58 mmol) in THF (5 ml) was added, at -78° C., stirred for 1 h, and then warmed to room temperature and stirred for 16 h. Water (25 ml) and dichloromethane (70 ml) were added and the aqueous extracted with dichloromethane (3×100 ml). The combined extracts were dried (Na2SO4), evaporated, and the crude product chromatographed through silica-gel using dichloromethane/methanol (92:8) as eluant to give the title compound as a yellow liquid (0.1 g); (Found: M+ =293.1378; C14H19N3O4 requires M+ =293.1376); m/e 293 (M+); δ (360 MHz, CDCl3) 2.34 (1H, d, J=16 Hz, CH of CH2N); 2.82 (1H, s, CH-bridgehead); 3.05 (1H, dd, J=4.3 and 14.6 Hz, CH of CH2 --N); 3.18 (3H, s, OMe); 3.20 (1H, dd, J=3.3 and 8.5 Hz, CH of CH2 --N); 3.28 (1H, d, J=12.7 Hz, CH of CH2 --N); 3.34 (3H, s, OMe); 3.59 (3H, s, CO2Me); 3.67 (1H, d, J=10.8 Hz, CH of CH2 --N); 3.91 (1H, dd, J=3 and 12.7 Hz, CH of CH2 --N); 8.45 (1H, d, J=3.7 Hz, pyrazine-H); 8.51 (1H, dd, J=2.5 and 3.7 Hz, pyrazine-H); 8.58 (1H, d, J=2.5 Hz, pyrazine-H).

Workup

  1. stirringstirred for 1 h
  2. stirringstirred for 16 h
  3. extractionthe aqueous extracted with dichloromethane (3×100 ml)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customevaporated
  6. customthe crude product chromatographed through silica-gel

Sources & evidence

ORD record
ord-393a83d681534aec85fa2f6131e07fed
Source dataset
uspto-grants-1993_11
Patent number
US05260293

Reaction notes

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