Dimethylformamide → HCID 22640305, compound

HRID 2415380Notes

Reaction equation

HRID 2415380 reaction equation
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH:4]1[CH:12]1[C:24]2[NH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH2:15][CH2:14][N:13]1[C:25]1[N:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[CH:27][N:26]=1.CN(C=[O:43])C>>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([C:28]2[CH:27]=[N:26][C:25]([N:13]3[CH2:14][C:15]4[C:16](=[O:43])[C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=5[NH:23][C:24]=4[CH:12]3[CH:4]3[CH2:5][C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[O:3]3)=[N:30][CH:29]=2)=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 22640312HCID 22640312, compound

Product 1

HCID 22640305HCID 22640305, compound

Procedure

Sodium hydride (60% in mineral oil, 87 mg, 2.18 mmol) and 1-(2,3-dihydro-5-benzfuranyl)-2,3,4,9-tetrahydro-2-[5-(4-methoxyphenyl)-2-pyrimidinyl]-1H-β-carboline (450 mg, 0.95 mmol) (prepared as in Example 46) in DMF (30 mL, anhydrous) were stirred at room temperature for 30 min. Dry air was then bubbled through the solution for 16 h. Ethyl acetate (200 mL) was then added to the solution. The resulting mixture was washed with 10% NaCl solution, brine and then dried with MgSO4. The solvent was evaporated and the residue triturated with ethyl acetate to yield the product as a white solid.

Workup

  1. customDry air
  2. customwas then bubbled through the solution for 16 h
  3. additionEthyl acetate (200 mL) was then added to the solution
  4. washThe resulting mixture was washed with 10% NaCl solution, brine
  5. dry with materialdried with MgSO4
  6. customThe solvent was evaporated
  7. customthe residue triturated with ethyl acetate

Sources & evidence

ORD record
ord-eeb30e442c5e4191b5bb426987a2e727
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

Loading…