Triethylamine → HCID 54199777, compound

HRID 1459465Notes

Reaction equation

HRID 1459465 reaction equation
[Cl:1][C:2]1[C:12]([NH2:13])=[C:6]2[CH2:7][C:8]([CH3:11])([CH3:10])[O:9][C:5]2=[C:4]([C:14]2[O:18][N:17]=[C:16]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:15]=2)[CH:3]=1.Br[CH2:26][CH2:27][CH2:28][C:29]#[N:30].C(N(CC)CC)C>CN(C)C=O>[NH2:13][C:12]1[C:6]2[CH2:7][C:8]([CH3:10])([CH3:11])[O:9][C:5]=2[C:4]([C:14]2[O:18][N:17]=[C:16]([CH:19]3[CH2:20][CH2:21][N:22]([CH2:26][CH2:27][CH2:28][C:29]#[N:30])[CH2:23][CH2:24]3)[N:15]=2)=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 214124-BromobutyronitrileHCID 86753482HCID 86753482, compound

Product 1

HCID 54199777HCID 54199777, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of intermediate 5 (4 g), 4-bromobutanenitrile (2.2 g) and triethylamine (4.2 ml) in dimethylformamide (70 ml) was stirred for 2 hours at 70° C. The mixture was cooled and the solvent evaporated. The residue was partitioned between CH2Cl2 and NH3 /H2O. The organic layer was separated, dried over MgSO4, filtered and the solvent evaporated. The residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent evaporated. The residue was solidified in DIPE at 0° C., filtered and dried, yielding 1.89 g (38%) of 4-[5-(4-amino-5-chloro-2,3-dihydro-2,2-dimethyl-7-benzofuranyl)-1,2,4-oxadiazol-3-yl]-1-piperidinebutanenitrile (compound 3; mp. 151.4° C.).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent evaporated
  3. customThe residue was partitioned between CH2Cl2 and NH3 /H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  9. customThe pure fractions were collected
  10. customthe solvent evaporated
  11. customwas solidified in DIPE at 0° C.
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-b163a8e5388e415eb9ffb14a397cb318
Source dataset
uspto-grants-1998_12
Patent number
US05854261

Reaction notes

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