Triethylamine → 2-Furan-2-yl-N5-methyl-N5-{2-[methyl-(5-methyl-isoxazol-3-ylmethyl)-amino]-ethyl}-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine

HRID 1181307Notes

Reaction equation

HRID 1181307 reaction equation
Cl[CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]1[N:29]=[C:17]2[N:18]=[C:19]([N:23]([CH3:28])[CH2:24][CH2:25][NH:26][CH3:27])[N:20]=[C:21]([NH2:22])[N:16]2[N:15]=1.CCN(CC)CC>CC#N>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]1[N:29]=[C:17]2[N:18]=[C:19]([N:23]([CH3:28])[CH2:24][CH2:25][N:26]([CH3:27])[CH2:2][C:3]3[CH:7]=[C:6]([CH3:8])[O:5][N:4]=3)[N:20]=[C:21]([NH2:22])[N:16]2[N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27357633-(Chloromethyl)-5-methyl-1,2-oxazoleHCID 694334172-furan-2-yl-N5-methyl-N5-(2-methylamino-ethyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine

Product 1

HCID 112575762-Furan-2-yl-N5-methyl-N5-{2-[methyl-(5-methyl-isoxazol-3-ylmethyl)-amino]-ethyl}-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Chloromethyl-5-methyl-isoxazole (1.5 eq.) was directly added to a solution of 2-furan-2-yl-N5-methyl-N5-(2-methylamino-ethyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine (0.14 mmol) 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 7.90 (br s, 2H), 7.80 (d, J=1.0 Hz, 1H), 7.05 (d, J=3.6 Hz, 1 H), 6.68 (dd, J=3.6 Hz, 1.0 Hz, 1H), 6.30 (s, 1H), 3.65 (m, 2H), 3.20-2.75 (m, 4H), 2.5 (s, 3H), 2.35 (s, 3H), 2.3 (s, 3H) ppm. MS: m/z: 385 [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-159e0926de984512b58125faa4e8c92d
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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