Acetylglycine → 2-acetamido-N-(5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide

HRID 336414Notes

Reaction equation

HRID 336414 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=O)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br.[CH3:33][S:34]([C:37]1[CH:38]=[C:39]([C:43]2[N:48]3[N:49]=[C:50]([NH2:52])[N:51]=[C:47]3[CH:46]=[CH:45][CH:44]=2)[CH:40]=[CH:41][CH:42]=1)(=[O:36])=[O:35].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1.CO.C(Cl)(Cl)Cl>[C:1]([NH:4][CH2:5][C:6]([NH:52][C:50]1[N:51]=[C:47]2[CH:46]=[CH:45][CH:44]=[C:43]([C:39]3[CH:40]=[CH:41][CH:42]=[C:37]([S:34]([CH3:33])(=[O:36])=[O:35])[CH:38]=3)[N:48]2[N:49]=1)=[O:8])(=[O:3])[CH3:2]

Participants

9

Reactant 5

HCID 10972AcetylglycineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 591864375-(3-(Methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 591862872-acetamido-N-(5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamideYield 81.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-Acetylglycine (406 mg, 3.47 mmol, 5.00 equiv) in pyridine (10 mL) was added triphenylphosphine (910 mg, 3.47 mmol, 5.00 equiv) at 0° C. After 5 min, carbon tetrabromide (1.15 g, 3.47 mmol, 5.0 equiv) was added, and the resulting yellow solution was maintained at 0° C. for 1.5 h. 5-(3-(Methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.200 g, 0.693 mmol, 1 equiv) was then added to the reaction mixture at 0° C. After 5 min, the reaction mixture was warmed to 24° C. and stirred overnight. Saturated aqueous sodium bicarbonate solution (20 mL), chloroform, and methanol were sequentially added to the reaction mixture. The solution was concentrated, and the resulting residue was purified by flash column chromatography (10% methanol, 1% ammonium hydroxide in dichloromethane) to afford product as white solid (220 mg, 78% yield). 1H NMR (400 MHz, CD3OD) δ 8.65 (s, 1H), 8.29 (dd, J=7.9, 1.1 Hz, 1H), 8.08 (dd, J=7.9, 1.0 Hz, 1H), 7.85-7.70 (m, 2H), 7.66 (dd, J=8.9, 1.2 Hz, 1H), 7.36 (dd, J=7.2, 1.2 Hz, 1H), 4.17 (s, 2H), 3.22 (s, 3H), 2.04 (s, 3H).

Workup

  1. waitAfter 5 min
  2. temperaturethe reaction mixture was warmed to 24° C.
  3. concentrationThe solution was concentrated
  4. customthe resulting residue was purified by flash column chromatography (10% methanol, 1% ammonium hydroxide in dichloromethane)

Sources & evidence

ORD record
ord-140a3f644a104a5a8c7c19ef35a4b335
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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