1-Methylpiperazine → HCID 59186322, compound

HRID 336413Notes

Reaction equation

HRID 336413 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([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:4][CH:3]=1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>C(OCC)(=O)C>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:2]2[N:7]=[CH:6][C:5]([NH:8][C:9]3[N:27]=[C:12]4[CH:13]=[CH:14][CH:15]=[C:16]([C:17]5[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=5)[N:11]4[N:10]=3)=[CH:4][CH:3]=2)[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 59186467HCID 59186467, compound

Product 1

HCID 59186322HCID 59186322, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(6-fluoropyridin-3-yl)-5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (250 mg, 0.65 mmol) in 1-methylpiperazine (500 mg, 5 mmol) was heated at 140° C. After 16 h, the reaction mixture was diluted with ethyl acetate (100 mL). The resulting solution was washed with water, and the collected organic was concentrated. Purification by preparative thin layer chromatography afforded the desired product (101 mg). LCMS (ESI) m/z: 464.2. 1H NMR (400 MHz, CDCl3), δ: 8.69 (s, 1H), 8.30 (s, 1H), 8.16-8.14 (d, J=8 Hz, 1H), 8.03-8.01 (d, J=8 Hz, 1H), 7.81-7.67 (m, 2H), 7.50-7.45 (m, 2H), 6.97 (s, 1H), 6.68-6.64 (m 2H), 3.42-3.34 (m, 4H), 3.10 (s, 3H), 2.48-2.45 (m, 4H), 2.47 (s, 3H).

Workup

  1. washThe resulting solution was washed with water
  2. concentrationthe collected organic was concentrated
  3. customPurification by preparative thin layer chromatography

Sources & evidence

ORD record
ord-20211770755a4caea3d2f5b7fae99a12
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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