Dimethylformamide → HCID 22640303, compound

HRID 2415382Notes

Reaction equation

HRID 2415382 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][CH:34]=[CH:33][N:32]=2)=[CH:27][N:26]=1.CN(C=[O:41])C>>[N:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:28]1[CH:29]=[N:30][C:25]([N:13]2[CH2:14][C:15]3[C:16](=[O:41])[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=4[NH:23][C:24]=3[CH:12]2[CH:4]2[CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[O:3]2)=[N:26][CH:27]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 22640301HCID 22640301, compound

Product 1

HCID 22640303HCID 22640303, compound

Procedure

Sodium hydride (60% in mineral oil, 182 mg, 4.55 mmol) and 1-(2,3-dihydro-5-benzofuranyl)-2,3,4,9-tetrahydro-2-[5-(2-pyridinyl)-2-pyrimidinyl]-1H-β-carboline (16176-23) (882 mg, 1.98 mmol) (prepared as in Example 49) in DMF (30 mL, anhydrous) were stirred at room temperature for 30 min. Dry air then was bubbled through the reaction mixture for 16 h. Ethyl acetate (200 mL) was added, and the resulting mixture was washed with 10% NaCl solution, brine, and then dried with MgSO4. The reaction mixture solvent was evaporated and the residue triturated with ethyl acetate to yield the product as a white solid.

Workup

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

Sources & evidence

ORD record
ord-817107e19df048a98777e7951bfb655c
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

Loading…