2-(Furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine → HCID 11351635, compound

HRID 1181290Notes

Reaction equation

HRID 1181290 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:19]=[C:9]2[N:10]=[C:11](S(C)(=O)=O)[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=1.[Cl:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([Cl:35])[C:26]=1[C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28]>CC#N>[NH2:14][C:13]1[N:8]2[N:7]=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[N:19]=[C:9]2[N:10]=[C:11]([N:32]2[CH2:33][CH2:34][N:29]([C:27]([C:26]3[C:25]([Cl:35])=[CH:24][N:23]=[CH:22][C:21]=3[Cl:20])=[O:28])[CH2:30][CH2:31]2)[N:12]=1

Participants

4

Reactant 2

HCID 99708822-(Furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amineHCID 69433730HCID 69433730, compound

Product 1

HCID 11351635HCID 11351635, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Furan-2-yl-5-methanesulfonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (0.15 mmol; see Example 1(a) above) was suspended in 4 mL of CH3CN along with 3 eq. of (3,5-Dichloro-pyridin-4-yl)-piperazin-1-yl-methanone. The reaction mixture was stirred under reflux for 3 hours. It was then cooled to room temperature and concentrated under reduced pressure. The resulting crude product was purified by preparative HPLC using a mixture of aqueous CH3CN that has been buffered with 0.1% TFA. 1H NMR (DMSO-d6) δ 8.9 (s, 2H), 7.60 (d, J=1.0 Hz, 1H), 7.28 (br s, 2H), 7.22 (d, J=3.6 Hz, 1H), 6.68 (dd, J=3.6 Hz, 1.0 Hz, 1H), 2.2-3.2 (m, 8H). MS: m/z: 461 [M+H]+.

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting crude product was purified by preparative HPLC
  4. additiona mixture of aqueous CH3CN that

Sources & evidence

ORD record
ord-646f571e2b2e46bca2c80db951b3bfc6
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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