2-Bromopropiophenone → HCID 71153188, compound

HRID 872252Notes

Reaction equation

HRID 872252 reaction equation
Br[CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH3:12][C:13]1[C:14]2[N:15]([N:19]=[C:20]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH2:28])[CH:23]=3)[N:21]=2)[CH:16]=[CH:17][N:18]=1.C(N(CC)C(C)C)(C)C>C(O)C>[CH3:12][C:13]1[C:14]2[N:15]([N:19]=[C:20]([C:22]3[CH:27]=[CH:26][N:25]4[C:2]([CH3:11])=[C:3]([C:5]5[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:28]=[C:24]4[CH:23]=3)[N:21]=2)[CH:16]=[CH:17][N:18]=1

Participants

5

Reactant 3

HCID 164522-BromopropiophenoneHCID 81531DiisopropylethylamineHCID 71153196HCID 71153196, compound

Product 1

HCID 71153188HCID 71153188, compoundYield 18.05%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromopropiophenone (0.034 ml, 0.221 mmol) was added to a solution of 4-(8-methyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)pyridin-2-amine (0.025 g, 0.111 mmol) in Ethanol (2.2 ml) and the mixture was heated at 80° C. for 40 hours. LC/MS analysis of the reaction mixture indicates reaction approximately 40% complete. The reaction mixture was transferred to a microwave reaction tube and N,N-diisopropylethylamine (0.059 ml, 0.332 mmol) was added. The reaction mixture was heated at 110° C. under standard microwave conditions for 2 hours. LC/MS analysis indicates reaction completion. The reaction mixture was concentrated in vacuo. The crude product was purified by flash chromatography (silica gel; 30-100% EtOAc/hexanes) to afford a tan solid (0.007 g, 0.020 mmol, 18.05% yield). 1H NMR (400 MHz, METHANOL-d4) δ 8.76 (d, J=4.5 Hz, 1H), 8.51 (s, 1H), 8.42 (d, J=6.5 Hz, 1H), 8.08 (d, J=4.5 Hz, 1H), 7.90 (dd, J=7.2, 1.6 Hz, 1H), 7.82-7.75 (m, 2H), 7.52 (t, J=7.5 Hz, 2H), 7.42 (s, 1H), 2.97 (s, 3H), 2.73 (s, 3H), LC/MS: (Method 2) Anal. Calcd. for [M+H]+C20H17N6: 341.15. Found: 341.07.

Workup

  1. customreaction approximately 40% complete
  2. additionwas added
  3. temperatureThe reaction mixture was heated at 110° C. under standard microwave conditions for 2 hours
  4. customreaction completion
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. customThe crude product was purified by flash chromatography (silica gel; 30-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-569e08b9234547d6ae85ddb4f9926e5c
Source dataset
uspto-grants-2015_03
Patent number
US08975276B2

Reaction notes

Loading…