Dimethylformamide → HCID 68428691, compound

HRID 2191306Notes

Reaction equation

HRID 2191306 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C:13]2[CH:16]=[CH:17][C:18](F)=[N:19][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][CH:22]([SH:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:1]([N:8]1[C:14](=[O:15])[C:13]2[CH:16]=[CH:17][C:18]([S:24][CH:22]([CH3:23])[CH3:21])=[N:19][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 63642-PropanethiolHCID 11430Potassium CarbonateHCID 59568636HCID 59568636, compound

Product 1

HCID 68428691HCID 68428691, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound obtained in Example 28, step 1 (0.50 g), isopropylthiol (0.20 potassium carbonate (0.51 g) and DMF (10 mL) was stirred at room temperature for 15 hr. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed twice with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane) to give 4-benzyl-8-(isopropylthio)-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one (0.38 g, 63%) as a white powder.

Workup

  1. extractionthe resulting product was extracted with ethyl acetate
  2. washThe organic layer was washed twice with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4ccd5a05e7b8415daed6fdc4911b2c41
Source dataset
uspto-grants-2012_12
Patent number
US08329687B2

Reaction notes

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