Triethylamine → 2-[6-(1H-Pyrazol-1-yl)-2-pyridyl]-4H-1,3-benzothiazine-4-one

HRID 748274Notes

Reaction equation

HRID 748274 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[C:14](OC)(=[O:22])[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[SH:17].C(N(CC)CC)C>C1(C)C=CC=CC=1>[N:1]1([C:6]2[N:11]=[C:10]([C:12]3[S:17][C:16]4[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=4[C:14](=[O:22])[N:13]=3)[CH:9]=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 229395546-(1H-pyrazol-1-yl)pyridine-2-carbonitrile

Product 1

HCID 597503912-[6-(1H-Pyrazol-1-yl)-2-pyridyl]-4H-1,3-benzothiazine-4-oneYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-(Pyrazol-1-yl)-2-pyridinecarbonitrile (0.68 g, 4.0 mmol) and methyl thiosalicylate (1.00 g, 5.9 mmol) were dissolved in toluene (5 ml), and triethylamine (2.0 ml, 14.3 mmol) was added thereto. The mixture was refluxed for 8 hrs. After cooling, the precipitates were collected by filtration and recrystallized from hexane-tetrahydrofuran to give the titled compound (0.82 g, 67%) as pale yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 8 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitates were collected by filtration
  4. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-bebaed22ff5e41f494ab2b6b84b1436b
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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