Peracetic Acid → 2-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-2-oxo-acetamide

HRID 886557Notes

Reaction equation

HRID 886557 reaction equation
C([CH:3]([C:9]1[CH:14]=[C:13]([C:15]2[CH:16]=[C:17]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH3:31])=[CH:22][N:21]([S:32]([C:35]4[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=4)(=[O:34])=[O:33])[C:18]3=[N:19][CH:20]=2)[N:12]=[CH:11][N:10]=1)[C:4]([N:6]([CH3:8])[CH3:7])=[O:5])#N.C(OO)(=[O:44])C.S(=O)(O)[O-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[CH3:31][O:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:23]1[C:17]2[C:18](=[N:19][CH:20]=[C:15]([C:13]3[N:12]=[CH:11][N:10]=[C:9]([C:3](=[O:44])[C:4]([N:6]([CH3:8])[CH3:7])=[O:5])[CH:14]=3)[CH:16]=2)[N:21]([S:32]([C:35]2[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=2)(=[O:34])=[O:33])[CH:22]=1

Participants

7

Reactant 4

HCID 6585Peracetic AcidHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 598249952-cyano-2-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-acetamide

Product 1

HCID 598250612-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-2-oxo-acetamideYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Cyano-2-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-acetamide (500 mg, 0.88 mmole) was suspended in tetrahydrofuran (11 mL) and cooled to 0° C. in an ice bath. Peroxy acetic acid (32% in acetic acid, 174 mg, 2.29 mmole) was added and after 10 min, the heterogeneous solution was removed from the ice bath and maintained at ambient temperature for 6 h. Sodium bisulfite (918 mg, 8.83 mmole) in water (10 mL) was added, followed by saturated aqueous sodium bicarbonate (20 mL) and the mixture extracted with ethyl acetate (3×30 mL). The combined organic portions were dried over magnesium sulfate, filtered, and concentrated to dryness. Silica gel chromatography of the crude residue afforded 2-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-2-oxo-acetamide (315 mg, 89% yield) as a clear residue. MS: m/z 402.2 (M+H+).

Workup

  1. customthe heterogeneous solution was removed from the ice bath
  2. temperaturemaintained at ambient temperature for 6 h
  3. extractionthe mixture extracted with ethyl acetate (3×30 mL)
  4. dry with materialThe combined organic portions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-eb3bb264e3b845848ff9fe838d3e4b39
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

Loading…