Ethylene Glycol → 2-[2-Amino-5-(4-methanesulfonylamino-phenyl)-pyridin-3-yloxymethyl]-benzoic acid

HRID 425939Notes

Reaction equation

HRID 425939 reaction equation
[OH-:1].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=2)=[CH:6][C:5]=1[O:21][CH2:22][C:23]1C=[CH:27][CH:26]=[CH:25][C:24]=1C#N.[CH2:31]([OH:34])[CH2:32]O>>[NH2:3][C:4]1[C:5]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:32]=2[C:31]([OH:34])=[O:1])=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=2)=[CH:8][N:9]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 21111366N-{4-[6-Amino-5-(2-cyano-benzyloxy)-pyridin-3-yl]-phenyl}-methanesulfonamide

Product 1

HCID 588866172-[2-Amino-5-(4-methanesulfonylamino-phenyl)-pyridin-3-yloxymethyl]-benzoic acid

Procedure

10% NaOH solution (25 mL) was added to N-{4-[6-amino-5-(2-cyano-benzyloxy)-pyridin-3-yl]-phenyl)methanesulfonamide (Example I-135, 650 mg, 1.65 mmol) in ethylene glycol (55 mL). The mixture was heated to reflux and allowed to stir for 24 hr. The reaction was cooled to room temperature. Most of the solvent was evaporated and the mixture was acidified. The precipitated solid was filtered out to afford 2-[2-Amino-5-(4-methanesulfonylamino-phenyl)-pyridin-3-yloxymethyl]-benzoic acid as light brown solid. The filtrate was neutralized and extracted with EtOAc (5×20 mL). The organic layer was combined, dried over MgSO4, and concentrated to yield 2-[2-Amino-5-(4-methanesulfonylamino-phenyl)-pyridin-3-yloxymethyl]-benzamide as an off-white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customMost of the solvent was evaporated
  4. filtrationThe precipitated solid was filtered out

Sources & evidence

ORD record
ord-916310e59a7d4f3fa0f1bb77a862c17b
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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