Dimethylformamide → HCID 87939624, compound

HRID 892107Notes

Reaction equation

HRID 892107 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15]3=[N:17][C@H:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:19][N:14]3[C:13](=[O:27])[N:12]([CH2:28][CH2:29][CH3:30])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].CN(C)[CH:41]=[O:42].[Cl-].[NH4+]>O1CCCC1.C1CCCCC1>[CH2:1]([N:8]1[C:16]2[C:15]3=[N:17][C@H:18]([CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:19][N:14]3[C:13](=[O:27])[N:12]([CH2:28][CH2:29][CH3:30])[C:11]=2[N:10]=[C:9]1[CH:41]=[O:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 23600250HCID 23600250, compound

Product 1

HCID 87939624HCID 87939624, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

Compound 35a (3.45 g, 8.96 mmol) obtained in Example 35 was dissolved in tetrahydrofuran (100 mL), to the solution was added a 1.50 mol/L solution (9.0 mL) of lithium diisopropylamide (13.5 mmol, 1.5 equivalents) in cyclohexane at −78° C., and the mixture was stirred for 1 hour. To the reaction solution was added a solution (10 mL) of N,N-dimethylformamide (2.83 g, 38.7 mmol, 4.3 equivalents) in tetrahydrofuran, and the mixture was stirred at −78° C. for 1 hour, then warmed to room temperature and stirred for 1 hour. To the reaction solution was added saturated aqueous ammonium chloride and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=33:67 to 50:50). To the residue was added ethyl acetate, and the deposited crystals were collected by filtration to obtain the title compound (3.31 g, 89%) as white crystals.

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 hour
  2. stirringstirred for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=33:67 to 50:50)
  8. additionTo the residue was added ethyl acetate
  9. filtrationthe deposited crystals were collected by filtration

Sources & evidence

ORD record
ord-1cc38df40bd34471baf7dc0e97a540ad
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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