Triethylamine → HCID 23074650, compound

HRID 730418Notes

Reaction equation

HRID 730418 reaction equation
[CH:1]([N:14]1[C:18]2=[N:19][C:20]([CH3:24])=[CH:21][C:22]([CH3:23])=[C:17]2[C:16]([C:25]#[N:26])=[C:15]1/[CH:27]=[CH:28]/[C:29]([O-:31])=O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:38][C:39]([CH3:44])([CH3:43])[CH2:40][CH2:41][NH2:42].C(N(CC)CC)C>C1COCC1.O.CN(C=O)C>[CH:1]([N:14]1[C:18]2=[N:19][C:20]([CH3:24])=[CH:21][C:22]([CH3:23])=[C:17]2[C:16]([C:25]#[N:26])=[C:15]1/[CH:27]=[CH:28]/[C:29]([NH:42][CH2:41][CH2:40][C:39]([CH3:44])([CH3:43])[CH3:38])=[O:31])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 197093,3-DimethylbutylamineHCID 65578Oxalyl chlorideHCID 23074653HCID 23074653, compound

Product 1

HCID 23074650HCID 23074650, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2E)-3-(1-benzhydryl-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl)propenoate (200 mg, 0.506 mmol) in THF (2 ml) were added DMF (0,01 ml) and oxalylchloride (0.053 ml, 0.607 mmol), the mixture was stirred at room temperature 1 hour, and the solvent was distilled off under reduced pressure. The residue was added under ice-cooling to a solution of 3,3-dimethylbutylamine (0.103 mg, 0.760 mmol), triethylamine (0.177 ml, 1.27 mmol) and THF (4 ml), and the mixture was stirred under ice-cooling for 1 hour. After stirring at room temperature for 4 hours, the reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the objective product as a solid material. The resultant material was recrystallized from hexane and ethyl acetate.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionThe residue was added under ice-
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 1 hour
  5. stirringAfter stirring at room temperature for 4 hours
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-bae1c7dc619f438292a0b68bc3bf8c97
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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