Triethylamine → 7-Furan-2-yl-N2-[1-(5-methyl-isoxazol-3-ylmethyl)-pyrrolidin-2-ylmethyl]-pyrazolo[1,5-a][1,3,5]triazine-2,4-diamine

HRID 1181305Notes

Reaction equation

HRID 1181305 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[CH:30]=[C:17]2[N:18]=[C:19]([NH:23][CH2:24][CH:25]3[CH2:29][CH2:28][CH2:27][NH:26]3)[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[CH:30]=[C:17]2[N:18]=[C:19]([NH:23][CH2:24][CH:25]3[CH2:29][CH2:28][CH2:27][N:26]3[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 694307307-Furan-2-yl-N2-pyrrolidin-2-ylmethyl-pyrazolo[1,5-a][1,3,5]triazine-2,4-diamine

Product 1

HCID 112231477-Furan-2-yl-N2-[1-(5-methyl-isoxazol-3-ylmethyl)-pyrrolidin-2-ylmethyl]-pyrazolo[1,5-a][1,3,5]triazine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Chloromethyl-5-methyl-isoxazole (1.5 eq.) was directly added to a solution of 7-furan-2-yl-N2-pyrrolidin-2-ylmethyl-pyrazolo[1,5-a][1,3,5]triazine-2,4-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 7.60 (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), 6.3 (s, 1H) 3.8 (br s, 2H), 2.2-3.2 (m, 8H), 1.6 (br s, 3 H). 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-798185b1bb5b4e26ad169c03c28f04e8
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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