Pyridine → HCID 69060955, compound

HRID 730461Notes

Reaction equation

HRID 730461 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:13])=[CH:9][C:10]=2[CH3:12])[N:5]([C@@H:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)[C:4]=1/[CH:24]=[CH:25]/[C:26]([OH:28])=O)#[N:2].C(Cl)(=O)C(Cl)=O.[CH3:35][C:36]([NH:38][C:39]1[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=1)=[O:37].N1C=CC=CC=1>C1COCC1.O.CN(C=O)C>[C:36]([NH:38][C:39]1[CH:44]=[CH:43][C:42]([NH:45][C:26](=[O:28])/[CH:25]=[CH:24]/[C:4]2[N:5]([C@@H:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16][CH2:15]3)[C:6]3=[N:7][C:8]([CH3:13])=[CH:9][C:10]([CH3:12])=[C:11]3[C:3]=2[C:1]#[N:2])=[CH:41][CH:40]=1)(=[O:37])[CH3:35]

Participants

8

Reactant 4

HCID 1049PyridineHCID 312304-AminoacetanilideHCID 65578Oxalyl chlorideHCID 69057218(2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl]prop-2-enoic acid

Product 1

HCID 69060955HCID 69060955, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (300 mg, 0.808 mmol) in THF (3 ml) were added DMF (0.03 ml) and oxalylchloride (0.0846 ml, 0.970 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 4-amino acetanilide (145 mg, 0.968 mmol), pyridine (0.262 ml, 3.24 mmol) and THF (3 ml), and the mixture was stirred under ice-cooling for 2 hours and at room temperature for 12 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 recrystallized from 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 2 hours and at room temperature for 12 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 recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-704c4e6e69314f9898f324ecd63818b0
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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