Triethylamine → HCID 19423605, compound

HRID 743057Notes

Reaction equation

HRID 743057 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][N:7]1[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:23].Br[CH2:25][C:26]#[N:27].C(N(CC)CC)C>CN(C)C=O.O>[C:26]([CH2:25][N:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][N:7]1[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:23])#[N:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11534BromoacetonitrileHCID 19423539HCID 19423539, compound

Product 1

HCID 19423605HCID 19423605, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 203 mg (0.66 mmol) of 3-(pyrrolidin-2-yl)methyl-4-phenyl-3,4-dihydro-2(1H)-quinazolinone, 95 mg (0.79 mmol) of bromoacetonitrile and 283 mg (2.8 mmol) of triethylamine in 5 mL of dimethyl-formamide was stirred for 6 hours at 70° C. After being cooled, the reaction mixture was diluted with water, and the mixture was extracted with chloroform. The organic layer separated was washed with water, dried on potassium carbonate and concentrated in vacuo. The residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform) to give 226 mg (0.65 mmol) of the title compound as an about 1:2 mixture of the diastereomers.

Workup

  1. temperatureAfter being cooled
  2. extractionthe mixture was extracted with chloroform
  3. customThe organic layer separated
  4. washwas washed with water
  5. customdried on potassium carbonate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform)

Sources & evidence

ORD record
ord-bae9e072927c4aecab048496565cbd2b
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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