Hydrochloric Acid → 2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]acetamide

HRID 1821900Notes

Reaction equation

HRID 1821900 reaction equation
Cl.[NH2:2][O:3][CH2:4][C:5]([NH2:7])=[O:6].[C:8]1([C:14]([C:16]2[NH:24][C:19]3=[CH:20][N:21]=[CH:22][CH:23]=[C:18]3[CH:17]=2)=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCO>[C:8]1([C:14](=[N:2][O:3][CH2:4][C:5]([NH2:7])=[O:6])[C:16]2[NH:24][C:19]3=[CH:20][N:21]=[CH:22][CH:23]=[C:18]3[CH:17]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 139561842-(Aminooxy)acetamideHCID 57893467phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

Product 1

HCID 1363865152-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]acetamideYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 N HCl (0.67 mL, 0.67 mmol) was added to a solution of 2-(aminooxy)acetamide (Reference Example 18) (90.5 mg, 1.04 mmol) in EtOH (6.7 mL) followed by addition of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 35) (150 mg, 0.67 mmol). The reaction mixture was refluxed overnight. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was free based using an SCX-2 and purified by Biotage chromatography to isolate 2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]acetamide (72.9 mg, 37%) as a white solid (single isomer, geometry of the oxime double bond undefined): Rf 0.13 (90:10 methylene chloride/methanol); 1H NMR (500 MHz, DMSO-d6) δ4.65 (2H, s), 6.65 (1H, s), 7.41-7.58 (8H, m), 8.14-8.15 (1H, d, J=5.5 Hz), 8.89 (1H, s), 12.01 (1H, br s); ESI MS m/z 295 [C16H14N4O2+H]+; HPLC (Method A) 98.9% (AUC), tR=14.8 min.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customthe solvent was removed in vacuo
  3. custompurified by Biotage chromatography

Sources & evidence

ORD record
ord-20fa7ca29bf54c44bfa1dbb60daa258b
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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