Triethylamine → 2-Furan-2-yl-5-[4-(5-methyl-isoxazol-3-ylmethyl)-piperazin-1-yl]-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

HRID 1181287Notes

Reaction equation

HRID 1181287 reaction equation
S([O-])(=O)(=O)C.[CH3:6][C:7]1[O:11][N:10]=[C:9]([CH2:12]OS(C)(=O)=O)[CH:8]=1.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[N:38]=[C:26]2[N:27]=[C:28]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[N:29]=[C:30]([NH2:31])[N:25]2[N:24]=1.CCN(CC)CC>CC#N>[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[N:38]=[C:26]2[N:27]=[C:28]([N:32]3[CH2:37][CH2:36][N:35]([CH2:12][C:9]4[CH:8]=[C:7]([CH3:6])[O:11][N:10]=4)[CH2:34][CH2:33]3)[N:29]=[C:30]([NH2:31])[N:25]2[N:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85257MethanesulfonateHCID 114490312-Furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamineHCID 57476926Methanesulfonic acid 5-methyl-isoxazol-3-ylmethyl ester

Product 1

HCID 111881932-Furan-2-yl-5-[4-(5-methyl-isoxazol-3-ylmethyl)-piperazin-1-yl]-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mesylate derivative from subpart (a) above (0.28 mmol) 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 temperature 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.

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-c71fd56e090c492ab1642de83a7b04ab
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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