Dimethylformamide → HCID 67279754, compound

HRID 1524338Notes

Reaction equation

HRID 1524338 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[CH2:11][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:14][O:15][C:16]=3[N:17]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O.C(OCC)(=O)C>[CH2:36]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10]3[CH2:11][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:14][O:15][C:16]=3[N:17]=2)[CH2:2][CH2:3]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67279638HCID 67279638, compound

Product 1

HCID 67279754HCID 67279754, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the compound (0.28 g) obtained in Example 33, step 1, potassium carbonate (0.23 g) and DMF (5 mL) was added benzyl bromide (109 μL), and the mixture was stirred at room temperature for 18 hr. Ethyl acetate and water were added to the reaction mixture. The organic layer was washed with water and brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→30% ethyl acetate/hexane) to give tert-butyl 8-(4-benzylpiperazin-1-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.24 g, 68%) as a white powder.

Workup

  1. washThe organic layer was washed with water and brine
  2. customdried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (solvent gradient; 0→30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-db37fb72a8684ac2b48ed994c6bf5dea
Source dataset
uspto-grants-2015_07
Patent number
US09079907B2

Reaction notes

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