Triethylamine → HCID 69059622, compound

HRID 730435Notes

Reaction equation

HRID 730435 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[N:9]2[C:13]3=[N:14][C:15]([CH3:19])=[CH:16][C:17]([CH3:18])=[C:12]3[C:11]([C:20]#[N:21])=[C:10]2/[CH:22]=[CH:23]/[C:24]([OH:26])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:40][C:41]1([CH3:48])[CH2:46][CH:45]([NH2:47])[CH2:44][CH2:43][O:42]1.C(N(CC)CC)C>C1COCC1.O.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[N:9]2[C:13]3=[N:14][C:15]([CH3:19])=[CH:16][C:17]([CH3:18])=[C:12]3[C:11]([C:20]#[N:21])=[C:10]2/[CH:22]=[CH:23]/[C:24]([NH:47][CH:45]2[CH2:44][CH2:43][O:42][C:41]([CH3:48])([CH3:40])[CH2:46]2)=[O:26])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 38092032,2-dimethyltetrahydro-2H-pyran-4-amineHCID 69055515HCID 69055515, compound

Product 1

HCID 69059622HCID 69059622, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2E)-3-{1-[bis(4-fluorophenyl)methyl]-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (300 mg, 0.677 mmol) in THF (3 ml) were added DMF (0.03ml) and oxalylchloride (0.071 ml, 0.813 mmol), the mixture was stirred at room temperature for 1 hour and the solvent was distilled off under reduced pressure. The residue was added under ice-cooling to a solution of 2,2-dimethyltetrahydro-2H-pyran-4-ylamine (175 mg, 1.35 mmol), triethylamine (0.313 ml, 2.25 mmol) and THF (2 ml), and the mixture was stirred under ice-cooling for 2 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and 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=2:1) to give the objective product as a solid material.

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 2 hours
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5f33c23192a84d1db241247e6d608d69
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

Loading…