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

HRID 748452Notes

Reaction equation

HRID 748452 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]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][C:20]([OH:22])=O)[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]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][C:20]([NH2:33])=[O:22])[CH:13]=2)=[N:3]1

Participants

6

Reactant 4

HCID 223AmmoniumHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 597503013-[2-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]propionic acid

Product 1

HCID 597503963-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]propanamideYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-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 (0.15 g, 49%) 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-40804cc1e4354a5dbb30b5b923c92b6c
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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