Triethylamine → 5-[4-(3,5-Dichloro-pyridin-4-ylmethyl)-piperazin-1-yl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

HRID 1181289Notes

Reaction equation

HRID 1181289 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH2:8]Cl.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]1[N:31]=[C:19]2[N:20]=[C:21]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[N:22]=[C:23]([NH2:24])[N:18]2[N:17]=1.CCN(CC)CC>CC#N>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH2:8][N:28]1[CH2:27][CH2:26][N:25]([C:21]2[N:22]=[C:23]([NH2:24])[N:18]3[N:17]=[C:16]([C:12]4[O:11][CH:15]=[CH:14][CH:13]=4)[N:31]=[C:19]3[N:20]=2)[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 114490312-Furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamineHCID 226268533,5-Dichloro-4-(chloromethyl)pyridine

Product 1

HCID 114307365-[4-(3,5-Dichloro-pyridin-4-ylmethyl)-piperazin-1-yl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,5-Dichloro-4-chloromethyl-pyridine (1.5 eq.) was added to a solution of 2-furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (0.14 mmol; see Example 1(a) above) and Et3N (0.3 mmol) in 3 mL of CH3CN. The resulting reaction mixture was stirred at room temp for 18 hours. It was then concentrated and 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), 3.8 (br s, 2H), 2.2-3.2 (m, 8H). MS: m/z: 447 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationIt was then concentrated
  3. custompurified by preparative HPLC
  4. additiona mixture of aqueous CH3CN that

Sources & evidence

ORD record
ord-66cc9b71ce5a401387aeb4b549074275
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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