Triethylamine → 2-[4-(3,5-Dimethyl-isoxazol-4-ylmethyl)piperazin-1-yl]-7-furan-2-yl-pyrazolo[1,5-a][1,3,5]triazin-4-ylamine

HRID 1181300Notes

Reaction equation

HRID 1181300 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][O:6][C:7]=1[CH3:8].[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]1[CH:30]=[C:18]2[N:19]=[C:20]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:21]=[C:22]([NH2:23])[N:17]2[N:16]=1.CCN(CC)CC>CC#N>[CH3:9][C:4]1[C:3]([CH2:2][N:27]2[CH2:26][CH2:25][N:24]([C:20]3[N:21]=[C:22]([NH2:23])[N:17]4[N:16]=[C:15]([C:11]5[O:10][CH:14]=[CH:13][CH:12]=5)[CH:30]=[C:18]4[N:19]=3)[CH2:29][CH2:28]2)=[C:7]([CH3:8])[O:6][N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-HCID 69432521HCID 69432521, compound

Product 1

HCID 114522062-[4-(3,5-Dimethyl-isoxazol-4-ylmethyl)piperazin-1-yl]-7-furan-2-yl-pyrazolo[1,5-a][1,3,5]triazin-4-ylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Chloromethyl-3,5-dimethyl-isoxazole (1.5 eq.) was directly added to a solution of 7-furan-2-yl-2-piperazin-1-yl-pyrazolo[1,5-a][1,3,5]triazin-4-ylamine (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 7.60 (d, J=1.0 Hz, 1 H), 7.28 (br s, 2H), 7.22 (d, J=3.6 Hz, 1H), 6.68 (dd, J=3.6 Hz, 1.0 Hz, 1 H), 6.2 (s, 1H) 3.8 (br s, 2H), 2.2-3.2 (m, 8H), 1.6 (br s, 6H). MS: m/z: 395 [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-28f9b72868fa4362b36cfc89acda1290
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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