Ammonium → 3-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanamide

HRID 499633Notes

Reaction equation

HRID 499633 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([CH2:18][CH2:19][C:20]([OH:22])=O)[CH:15]=[CH:14][CH:13]=2)=[N:3]1.ClC(OCC(C)C)=O.C([N:33](CC)CC)C.[NH4+]>C1COCC1>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([CH2:18][CH2:19][C:20]([NH2:33])=[O:22])[CH:15]=[CH:14][CH:13]=2)=[N:3]1

Participants

6

Reactant 4

HCID 223AmmoniumHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 99013333-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propionic acid

Product 1

HCID 597502893-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanamideYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propionic acid (0.31 g, 1.00 mmol), isobutyl chloroformate (0.22 ml, 1.50 mmol) and triethylamine (0.22 ml, 1.50 mmol) were dissolved in THF (10 ml), and the mixture was stirred under ice cooling condition for 1 hr. 25% aqueous ammonium solution was added to the mixture, and the mixture was stirred under ice cooling condition for 0.5 hr. The obtained precipitates were recrystallized from ethanol to give the titled compound (0.20 g, 65%) as white crystals.

Workup

  1. stirringthe mixture was stirred under ice cooling condition for 0.5 hr
  2. customThe obtained precipitates
  3. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-0d24866be3b745eb8d8d2c0f1dbbb3cf
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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