Lawesson's reagent → 2-Methyl-N-(5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)thiazol-5-amine

HRID 336415Notes

Reaction equation

HRID 336415 reaction equation
[C:1]([NH:4][CH2:5][C:6]([NH:8][C:9]1[N:27]=[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=3)[N:11]2[N:10]=1)=O)(=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>>[CH3:2][C:1]1[S:37][C:6]([NH:8][C:9]2[N:27]=[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=4)[N:11]3[N:10]=2)=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 591862872-acetamido-N-(5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide

Product 1

HCID 591861982-Methyl-N-(5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)thiazol-5-amineYield 43.2%

Procedure

A solution of 2-acetamido-N-(5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide (46 mg, 0.12 mmol, 1 equiv) and Lawesson's reagent (190 mg, 0.48 mmol, 4.0 equiv) was heated under reflux for 6 hr. The reaction mixture was concentrated in vacuo, and the resulting residue was diluted with water and ethyl acetate. The product was collected by filtration and purified by preparative HPLC to afford product (20 mg, 40% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.41 (s, 1H), 8.71 (t, J=1.6 Hz, 1H), 8.35 (s, 1H), 8.11 (s, 1H), 7.90 (d, J=7.9 Hz, 1H), 7.71 (d, J=7.2 Hz, 1H), 7.60 (m, 1H), 7.37 (dd, J=7.2, 1.3 Hz, 1H), 7.28 (s, 1H), 3.33 (s, 3H), 2.52 (s, 3H).

Workup

  1. temperatureunder reflux for 6 hr
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe resulting residue was diluted with water and ethyl acetate
  4. filtrationThe product was collected by filtration
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-131896f5e9064494adbd155c1ce65fe7
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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